One-Pot Catalytic Enantioselective Synthesis of Functionalized Tetrahydroquinolines by Aza-Michael/Michael Cascade Reactions of N-Protected 2-Aminophenyl alpha,beta-Unsaturated Esters with Nitroolefins

A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl ,-unsaturated esters in the presence of a chiral...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 46; no. 24; pp. 3365 - 3373
Main Authors Kang, Ki-Tae, Kim, Sung-Gon
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 15.12.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MICHAEL REACTION
ACTIVATION
Michael additions
QUINOLINES
TRANSFER HYDROGENATION
3-COMPONENT POVAROV REACTION
DISCOVERY
organocatalysis
cascade reactions
tetrahydroquinolines
asymmetric synthesis
BIFUNCTIONAL THIOUREA
THIOUREA ORGANOCATALYSTS
ASYMMETRIC ORGANOCATALYSIS
INHIBITORS
Online AccessGet more information

Cover

More Information
Summary:A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl ,-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (99% ee).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1379044