Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic...
Transcript of Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic...
![Page 1: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/1.jpg)
Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly
diastereoselective Ugi multicomponent reaction
Valentina Cerulli, Luca Banfi, Andrea Basso, Valeria Rocca, Renata Riva
Supporting Information
1H AND
13C NMR SPECTRA OF NEW COMPOUNDS (PART II)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 36a
O O
N
O
O
HN
36a
3a
46
6a
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 36a
O O
N
O
O
HN
36a
3a
46
6a
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 37a
O O
N
O
O
HN
37a
3a
46
6a
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 37a
O O
N
O
O
HN
37a
3a
46
6a
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 6: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/6.jpg)
1H NMR of compound 38a
HO OH
N
O
O
HN
Bn
MeO
38a
3a
46
6a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 38a
HO OH
N
O
O
HN
Bn
MeO
38a
3a
46
6a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 39a
N
O
OO
39a
HN
O
O
OTBDMS
MeO
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 9: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/9.jpg)
13C NMR of compound 39a
N
O
OO
39a
HN
O
O
OTBDMS
MeO
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 39b
N
O
OO
39b
HN
O
O
OTBDMS
MeO
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 39b
N
O
OO
39b
HN
O
O
OTBDMS
MeO
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 40a
N
O
OO
40a
HN
O
O
OTBDMS
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 13: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/13.jpg)
13C NMR of compound 40a
N
O
OO
40a
HN
O
O
OTBDMS
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 14: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/14.jpg)
1H NMR of compound 40c
N
O
OO
40c
HN
O
O
OTBDMS
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 40c
N
O
OO
40c
HN
O
O
OTBDMS
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 16: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/16.jpg)
1H NMR of compound 41a
N
O
OO
41a
H
N
O
O
OTBDMS
Br
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 41a
N
O
OO
41a
H
N
O
O
OTBDMS
Br
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 41c
N
O
OO
41c
HN
O
O
OTBDMS
Br
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 41c
N
O
OO
41c
HN
O
O
OTBDMS
Br
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 42a
N
O
OO
42a
H
N
O
O
OTBDMS
Br
S
Cl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 42a
N
O
OO
42a
H
N
O
O
OTBDMS
Br
S
Cl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 42c
N
O
OO
42c
H
N
O
O
OTBDMS
Br
S
Cl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 42c
N
O
OO
42c
H
N
O
O
OTBDMS
Br
S
Cl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 24: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/24.jpg)
1H NMR of compound 43a
N
O
OO
43a
H
N
O
O
OTBDMS
Br
ZHN
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 43a
N
O
OO
43a
H
N
O
O
OTBDMS
Br
ZHN
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 26: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/26.jpg)
1H NMR of compound 43c
N
O
OO
43c
H
N
O
O
OTBDMS
Br
ZHN
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 43c
N
O
OO
43c
H
N
O
O
OTBDMS
Br
ZHN
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 28: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/28.jpg)
1H NMR of compound 44a
N
O
OO
44a
H
N
O
Ph
OTBDMS
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 44a
N
O
OO
44a
H
N
O
Ph
OTBDMS
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 44b
N
O
OO
44b
H
N
O
Ph
OTBDMS
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 44b
N
O
OO
44b
H
N
O
Ph
OTBDMS
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 45c
N
O
OO
45c
H
N
O
Ph
OTBDMS
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 33: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/33.jpg)
13C NMR of compound 45c
N
O
OO
45c
H
N
O
Ph
OTBDMS
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 34: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/34.jpg)
1H NMR of compound 46c
N
O
OO
46c
H
N
O
Ph
OTBDMS
SCl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 46c
N
O
OO
46c
H
N
O
Ph
OTBDMS
SCl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 47a
N
O
OO
H
N
O
O
OH
Br
MeO
47a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 47a
N
O
OO
H
N
O
O
OH
Br
MeO
47a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 48a
N
O
OO
HN
O
O
OH
Br
48a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 48a
N
O
OO
HN
O
O
OH
Br
48a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 48c
N
O
OO
H
N
O
O
OH
Br
48c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 48c
N
O
OO
H
N
O
O
OH
Br
48c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 49a
N
O
OO
H
N
O
O
OH
Br
49a
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 49a
N
O
OO
H
N
O
O
OH
Br
49a
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 50a
N
O
OO
H
N
O
O
OH
Br
50a
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 50a
N
O
OO
H
N
O
O
OH
Br
50a
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 50c
N
O
OO
HN
O
O
OH
Br
50c
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 50c
N
O
OO
HN
O
O
OH
Br
50c
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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1H NMR of compound 51a
N
O
OHHO
H
N
O
O
OH
Br
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 51a
N
O
OHHO
H
N
O
O
OH
Br
MeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 50: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/50.jpg)
1H NMR of compound 51c
N
O
OHHO
H
N
O
O
OH
Br
MeO
51c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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13C NMR of compound 51c
N
O
OHHO
H
N
O
O
OH
Br
MeO
51c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 52: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/52.jpg)
1H NMR of compound 52a
N
O
OHHO
HN
O
O
OH
Br
52a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 53: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/53.jpg)
13C NMR of compound 52a
N
O
OHHO
HN
O
O
OH
Br
52a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 54: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/54.jpg)
1H NMR of compound 53a
N
O
OHHO
H
N
O
O
OH
Br
53a
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 55: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/55.jpg)
13C NMR of compound 53a
N
O
OHHO
H
N
O
O
OH
Br
53a
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 56: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/56.jpg)
1H NMR of compound 54a
N
O
OHHO
H
N
O
O
OH
Br
54a
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 57: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/57.jpg)
13C NMR of compound 54a
N
O
OHHO
H
N
O
O
OH
Br
54a
NH
Z
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 58: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/58.jpg)
1H NMR of compound 55a
N
O
OO
55a
MeO
H
N
O
CO2Me
O
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 59: Diversity oriented and chemoenzymatic synthesis of densely ...Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective](https://reader030.fdocuments.in/reader030/viewer/2022040613/5f07d9f67e708231d41f120e/html5/thumbnails/59.jpg)
13C NMR of compound 55a
N
O
OO
55a
MeO
H
N
O
CO2Me
O
Br
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011