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A Highly Enantioselective Catalytic Domino Aza-Michael/Aldol Reaction: One-Pot Organocatalytic Asymmetric Synthesis of 1,2-Dihydroquinolidines

✍ Scribed by Henrik Sundén; Ramon Rios; Ismail Ibrahem; Gui-Ling Zhao; Lars Eriksson; Armando Córdova

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
188 KB
Volume
349
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

The highly enantioselective organocatalytic domino aza‐Michael/aldol reaction is presented. The unprecedented, chiral amine‐catalyzed asymmetric domino reactions between 2‐aminobenzaldehydes and α,β‐unsaturated aldehydes proceed with excellent chemo‐ and enantioselectivity to give the corresponding pharmaceutically valuable 1,2‐dihydroquinolines derivatives in high yields with 90 to >99 % ee.

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## Abstract An enantioselective oxa‐Michael–Henry reaction of substituted salicylaldehydes with nitroolefins that proceeds though an aromatic iminium activation (AIA) has been developed by using a chiral secondary amine organocatalyst and salicylic acid as a co‐catalyst. The corresponding 3‐nitro‐2