04/17/2010 Hidden Gems in Chemistry Letters · Chem. Lett., 2009, 38(2), 116 Ts N I SiMe3 Ts N Si O...
6
1 Jun Shi Baran Group Meeting 04/17/2010 • founded in 1972 • published by The Chemical Society of Japan monthly • first Editor-in-Chief: Teruaki Mukaiyama (633 papers)* • Tamejiro Hiyama: current editor-in-chief since 2003 • 39 volums, 461 issues, 22,143 papers • covers all areas of chemistry • highligh reviews since 2004 • 1.504-impact factor in 2008 1. Chem. Lett. 1972, 373/1972, 401 NH 2 MeOH CO,Se, Et 3 N, R.T. N H OMe O Et 2 NH THF CO, Se, heat O NEt 2 Et 2 N 2. Chem. Lett., 1973, 91 H Ph H NO 2 Benzene reflux Pd(OAc) 2 Ph Ph H NO 2 first example of phenylation of nitro-olefin 70% 3. Chem. Lett., 1973, 1071 R H NNHTs PhN 2 Cl Ar N NNHTs NPh N N NPh N Ar NaOH synthesis of 2,5-disubstituted tetrazole 4. Chem. Lett., 1975, 1333 Bu 3 Sn NH 2 Me CH 2 isoamyl nitrite tBuCO 2 H 60°C Me CH 2 65% 5. Chem. Lett., 1976, 47 O N H Cl Br tBuOK PhNCO N Ph N O O Cl 78% -50°C 6. Chem. Lett., 1977, 471 N Ar O NHAr O S-CH-CO 2 Et then ClCO 2 Et " " HS-CH 2 -CO 2 Et 2 eq LDA O CO 2 Et 7. Chem. Lett., 1977, 553 CN CN Me Ph Cl 3 CCOOH THF, Et 3 N CN CN Ph Cl Cl Me 9. Chem. Lett. 1977, 569 O OH O O CO 2 Me O MeOH:AcOH 5 : 1 hν hν MeOH 10. Chem. Lett., 1980, 825 ArCH 2 NH 2 OH MeHN N O O 4-C 6 H 4 -Cl cat. air ArCHO O Ph Ph F F Me Me NaCO 2 CF 3 DMF, 170°C 8. Chem. Lett., 2005, 1440, 34(10) Chemistry Letters (1972-2010): "Hidden Gems" in Chemistry Letters reflux proposed mechanism in this paper: *No Prof. Mukaiyama's chemsitry in Chem. Lett. is included here. Please see Yoshi's GM on Mukaiyama instead FIY.
-
Upload
truongquynh -
Category
Documents
-
view
221 -
download
0
Transcript of 04/17/2010 Hidden Gems in Chemistry Letters · Chem. Lett., 2009, 38(2), 116 Ts N I SiMe3 Ts N Si O...
1
Jun ShiBaran Group Meeting04/17/2010
• founded in 1972• published by The Chemical Society of Japan monthly• first Editor-in-Chief: Teruaki Mukaiyama (633 papers)*• Tamejiro Hiyama: current editor-in-chief since 2003• 39 volums, 461 issues, 22,143 papers• covers all areas of chemistry• highligh reviews since 2004• 1.504-impact factor in 2008
1. Chem. Lett. 1972, 373/1972, 401
NH2MeOH
CO,Se, Et3N, R.T.NH
OMe
O
Et2NHTHF
CO, Se, heat
O
NEt2Et2N
2. Chem. Lett., 1973, 91
H
Ph H
NO2Benzenereflux
Pd(OAc)2
Ph
Ph H
NO2
first example of phenylation of nitro-olefin
70%
3. Chem. Lett., 1973, 1071
R H
NNHTs PhN2Cl
Ar N
NNHTs
NPh
N
NNPh
N
ArNaOH
synthesis of 2,5-disubstituted tetrazole
4. Chem. Lett., 1975, 1333Bu3Sn NH2
Me
CH2
isoamyl nitritetBuCO2H60°C
Me
CH2 65%
5. Chem. Lett., 1976, 47
O
NH
Cl
Br
tBuOKPhNCO
NPh
NOO
Cl
78%-50°C
6. Chem. Lett., 1977, 471
NAr
O
NHAr
O
S-CH-CO2Etthen ClCO2Et
" "HS-CH2-CO2Et2 eq LDA
O CO2Et
7. Chem. Lett., 1977, 553
CN
CNMe
Ph Cl3CCOOH
THF, Et3N
CN
CN
Ph
Cl ClMe
9. Chem. Lett. 1977, 569O
OH
OO
CO2MeO MeOH:AcOH
5 : 1hνhν
MeOH
10. Chem. Lett., 1980, 825
ArCH2NH2
OH
MeHN
N
O
O
4-C6H4-Cl
cat.
air ArCHO
O
Ph Ph
F FMe
MeNaCO2CF3
DMF, 170°C
8. Chem. Lett., 2005, 1440, 34(10)
Chemistry Letters (1972-2010):
"Hidden Gems" in Chemistry Letters
reflux
proposed mechanism in this paper:
*No Prof. Mukaiyama's chemsitry in Chem. Lett. is included here. Please see Yoshi's GM on Mukaiyama instead FIY.
2
Jun ShiBaran Group Meeting04/17/2010
11. Chem. Lett., 1982, 1933
NC CN
NEt2MeS
LDA, 60% N
S
H2N
NCNEt2
CN
NEt2
12.Chem. Lett., 1985, 291O
MeMe
S
NHCOPhPPA
120°C
O
MeMe
N
Ph
21. Chem. Lett., 1988, 589 "synthesis of diamond by CO and H2"
13. Chem. Lett., 1987, 5
SnBu3R SnBu3
Pd(OAc)2
tBuOOHR+
14. Chem. Lett., 1987, 809
PhSCONHPh
PhS
3 eq BuLi
E+
CONHPhPhS
E
15. Chem. Lett., 1987, 859
RRhCl(CO)(PMe3)2
CO, hνR
16. Chem. Lett., 1987, 899
CO2MeN
NCO2Me
tBu
tBuTsOHBezene, reflux
NCO2Me
tBu
tBu
17. Chem. Lett. 1987, 1145
R1 R2
O FCl2CCO2Me
R1 R2
F CO2Me
Zn(cat)-CuCl
18. Chem. Lett., 1987, 1569
Me
Me
SPh
EtO2C CO2Et
N2 Rh2(OAc)4
Tol. refluxMeMe
CO2Et
CO2Et
SPh
19. Chem. Lett., 1987, 1575
84.3%
N+O-
Ph PhSeOTf
DBUthenBzCl
NHBz
"Selenium Polonovski Reaction"
20 Chem. Lett., 1987, 1575R1
OTf
RMgBr
Li2MnCl4 cat.
R1
R
+
"Hidden Gems" in Chemistry Letters
3
Jun ShiBaran Group Meeting04/17/2010
22. Chem. Lett., 1990, 1125
Ar
OHR Ar
OR
Cl
TsNCl2MeCN, 35°C
23. Chem. Lett., 1992, 1161
NHO
Ac P(nBu)3-CCl4MeCN, R.T
NH
Ac
HO
75.6%
24. Chem. Lett., 1994, 627
"Transhydroxylation"
Me
OOEt
O
SiMe2Ph
Me
SnCl4, R.T.
OEtO2C
SiMe2Ph
MeMe
25. Chem. Lett., 1995, 679
OMe
OR
R = alkyl, SiR3O
Me
O
RRu(H)2(CO)(PPh3)3cat.
26. Chem. Lett., 1995, 681
O
R, R = alkyl, SiR3
Ru(H)2(CO)(PPh3)3cat.
R R'
OR'R
S
OMe
Ru(H)2(CO)(PPh3)3cat.
Ph SiMe3S
OMe
Ph
SiMe3
90%
27. Chem. Lett., 1997, 55
NC
NC CN
CNcat.
R OH
O
R2OH R OR2
O
30. Chem. Lett., 2004, 832, 33(7)
OMe
OMe
Ph
CoCl2(dpph) catTMSCH2MgCl(3 eq)
ether, reflux, 48h
PhTMS
90% TMS
31. Chem. Lett., 2005, 194, 34(2)
XMnO2, CHCl3
reflux O
32. Chem. Lett., 2006, 714, 35(7)
PhSiH3 + ROHCu(hfa)2 cat
F3C
O O
CF3
PhSiH2OR
hfa
"Hidden Gems" in Chemistry Letters
NC
NC CN
CNcat.
R OMe
O
R2OH R OR2
O
OMe
OMe
Ph
CoCl2(dpph) catTMSCH2MgCl(1.5 eq)
ether, 20°C, 35hOMe
PhTMS
85%
40%-99%
99-54%
75%
"Hidden Gems" in Chemistry Letters
4
Jun ShiBaran Group Meeting04/17/2010
33. Chem. Lett., 2007, 1414, 36 (12)
Ar
OH
Ar' Ar
O
Ar'
O2
Actived Carbon
34. Chem. Lett., 2007, 36(5), 636
F3CN O
O O 1) TMSOTf2) TiCl4,
N O
O OF
ClF
35. Chem. Lett., 2007, 366, 36(3)
O OSi
OSi
SiPhH
H
RhCl(PPh3)4
SiPhH
H
O
RhCl(PPh3)4
1,2-reduction
1,4-reduction
36. Chem. Lett. 2007, 52, 36(1)
R2
R1
N NH
R1
R2
Rh2(OOCCF3)4 cat
60°C
37. Chem. Lett., 2008, 1006
Ph
F3C
O
OBAr+
Ph
FF
[RhCl(cod)2]2
38. Chem. Lett., 2008, 786
ArHS+
SPh
-OS
SPh
ArTf2O
S+
SMe
Me-O
Tf2O
Me
2,6-di-tBuPyr.
2,6-di-tBuPyr.
SMeMeSMe
62%
40. Chem. Lett., 2009, 38(1), 46
PdCl2, CuCl, CO/O2
MeOH
CO2Me
CO2Me
41. Chem. Lett., 2009, 38(2), 116
TsN
I
SiMe3
TsN
Si OH2C
Me Me
MeMe
CH2(ZnI)2
NiCl2dppe
Acetone
Ar
O
60-79%
86%
75%
5
Jun ShiBaran Group Meeting04/17/2010
42. Chem. Lett. 2009, 38(3), 204
O O
CO2Me
Ar
RNC, Pd(PPh3)4 NR
Me
CO2Me
Ar
OMe Ni(cod)2/LNaOtBu NR1R2
43. Chem. Lett. 2009, 38(7), 710
NHR1R2RR
44. Chem. Lett. 2009, 38(5), 430
CHOR
H2O2
Pd(TFA)2CO2H
R
45. Chem. Lett. 2009, 38(5), 484
Het-CHOEt3N, ROH
Thiamine hydrochlorideHet-CO2R
46. Chem. Lett. 2009, 488
MeO2C
N2
O
O
O
OO H
MeO2C
O
47. Chem. Lett. 2009, 38(6), 352
ArSiMe
MeOH
TEMPONaOCl, KBr
ArSi
OH
Me
Me
Thiamine hydrochlorideHet: pyridines, quinolines, quinoxaline
X = F
Selected Total Syntheses:
1. Chem. Lett., 1990, 1230
O
OMeOMe
OOBn
MeO
MeOO
NBn
OOBn
ONBn
OMeOMe
OH
OBn
250°C
OOBn
NBn
OMeOMe
HO
(-)-Mesembrine
2. Chem. Lett., 2004, 942
OH
OTHP
Mn(pic)3
nBuSnH88%
THPOH
H O
H
HEtO2C
OH
HOCO2Et
H
H
CO2Et OOHCH
H
CO2H
OH
Sordarincin
Pd(PPh3)4NaH
"Hidden Gems" in Chemistry Letters
93 ee%, 71%
42-89%
75-96%
74-99%
"Hidden Gems" in Chemistry Letters
6
Jun ShiBaran Group Meeting04/17/2010
3. Chem. Lett., 2007, 10
MeO CHO
HO
MeO
MeOMeO2C
O
O
Me
O
MeO
MeOMeO2C
O
O
O
O Me
OMe
CO2MeOOMe
OMe
40%DTBMP200°C
HO
HOHO2C
O
O
O
O Me
OMe
CO2HOOH
OH
MeO
MeO
O
OBr
AlCl3100°C 74%
Carotenoid Radicals: Cryptochemistry of Natural Colorants
Formation of C–C Bonds via Ruthenium-catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level
Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions 2009, 8
2010,148
2008, 1102
Participation of Geminal Bonds in Organic Reactions 820, 2007
Catalytic Direct Arylation of Heteroaromatic Compounds 200, 2007
Alkyl Phosphinites: Versatile Synthetic Intermediates for Dehydration Condensation Reactions 2, 2007
Transition Metal-catalyzed Carbochalcogenation of Alkynes 1320, 2006
Cycloaddition Reactions of Transition Metal-containing Benzopyrylium and Related Zwitterionic Intermediates 1082, 2006
The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis824, 2006
Ruthenium-catalyzed Reconstructive Synthesis of Functional Organic Molecules via Cleavage of Carbon–Carbon Bonds 1462, 2005
Azide Compounds: Nitrogen Sources for Atom-efficient and Ecologically Benign Nitrogen-atom-transfer Reactions 1304, 2005
Transition Metal-catalyzed Reactions Using Alkynes as Precursors of Carbene and Vinylidene Complexes 1068, 2005
Advances in Iron Catalyzed Cross Coupling Reactions 624, 2005
Iminium Alkaloids from Marine Invertebrates: Structure, Biological Activity, and Biogenesis!Sulfoximines: Synthesis and Catalytic Applications 482, 2004
Palladium Catalyzed Aerobic Dehydrogenation: From Alcohols to Indoles and Asymmetric Catalysis 362, 2004
454, 2005
Selected Reviews:1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
vinaxathone
