Air- and moisture-tolerant Substrate scope extends to both aryl and aliphatic electrophiles
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Air- and moisture-tolerant Air- and moisture-tolerant Substrate scope extends to both aryl and aliphatic electrophiles Substrate scope extends to both aryl and aliphatic electrophiles Reaction selective for Reaction selective for N -acyl pyrroles (e.g. -acyl pyrroles (e.g. 2b 2b favored over favored over 2a 2a) Electronic tuning of the carbamate in 1 critical for Electronic tuning of the carbamate in 1 critical for nucleophilicity nucleophilicity Methodology a lead discovery point for new Br Methodology a lead discovery point for new Brø nsted acid nsted acid catalysts catalysts Investigation of Catalytic Methods for the Preparation of N-Heterocycles Anna G. Wenzel; W.M. Keck Science Center, Claremont CA 91711 A catalytic method for the preparation of dihydroquinolines utilizing copper triflate: H O N H C bz H O N H C bz R 1 R 2 O Michael Addition Aldol Condensation N C bz R 1 (±) 1 3a 3b + R 1 R 2 O 2a (R 1 = Ph,R 2 = H ) 2b (R 1 = Ph,R 2 = ) O R 2 N Cu(O Tf) 2 CH 3 CN Joint Science Department Claremont McKenna College ♦ Pitzer College ♦ Scripps College Members of the Claremont Colleges J S D
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Investigation of Catalytic Methods for the Preparation of N -Heterocycles. Anna G. Wenzel; W.M. Keck Science Center, Claremont CA 91711. Air- and moisture-tolerant Substrate scope extends to both aryl and aliphatic electrophiles - PowerPoint PPT Presentation
Transcript of Air- and moisture-tolerant Substrate scope extends to both aryl and aliphatic electrophiles
Air- and moisture-tolerantAir- and moisture-tolerant Substrate scope extends to both aryl and aliphatic electrophilesSubstrate scope extends to both aryl and aliphatic electrophiles Reaction selective for Reaction selective for NN-acyl pyrroles (e.g. -acyl pyrroles (e.g. 2b 2b favored overfavored over 2a 2a)) Electronic tuning of the carbamate in 1 critical for nucleophilicityElectronic tuning of the carbamate in 1 critical for nucleophilicity Methodology a lead discovery point for new BrMethodology a lead discovery point for new Brøønsted acid catalystsnsted acid catalysts
Investigation of Catalytic Methods for the Preparation of N-Heterocycles
Anna G. Wenzel; W.M. Keck Science Center, Claremont CA 91711
A catalytic method for the preparation of dihydroquinolines utilizing copper triflate:
H
O
NHCbz
H
O
NHCbz R1
R2
O
Michael Addition
Aldol Condensation
NCbz
R1(±)
1 3a3b
+
R1
R2
O
2a (R1 = Ph, R2 = H)2b (R1 = Ph, R2 = )
O
R2
N
Cu(OTf)2
CH3CN
Joint Science DepartmentClaremont McKenna College ♦ Pitzer College ♦ Scripps CollegeMembers of the Claremont Colleges
JSD
