A highly enantioselective catalytic domino aza-Michael/aldol reaction: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines

Henrik Sundén; Ramon Rios; Ismail Ibrahem; Gui Ling Zhao; Lars Eriksson; Armando Córdova

doi:10.1002/adsc.200600513

A highly enantioselective catalytic domino aza-Michael/aldol reaction: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines

Henrik Sundén
, Ramon Rios
, Ismail Ibrahem
, Gui Ling Zhao
, Lars Eriksson
, Armando Córdova

Chemistry

Arrhenius Laboratory

Research output: Contribution to journal › Article › peer-review

127 Scopus citations

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.

Original language	British English
Pages (from-to)	827-832
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	6
DOIs	https://doi.org/10.1002/adsc.200600513
State	Published - Apr 2007

Keywords

Asymmetric catalysis
Aza-Michael reaction
Domino reactions
Nitrogen heterocycles;α,βunsaturated aldehydes

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title = "A highly enantioselective catalytic domino aza-Michael/aldol reaction: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines",

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.",

keywords = "Asymmetric catalysis, Aza-Michael reaction, Domino reactions, Nitrogen heterocycles;α,βunsaturated aldehydes",

author = "Henrik Sund{\'e}n and Ramon Rios and Ismail Ibrahem and Zhao, \{Gui Ling\} and Lars Eriksson and Armando C{\'o}rdova",

year = "2007",

month = apr,

doi = "10.1002/adsc.200600513",

language = "British English",

volume = "349",

pages = "827--832",

journal = "Advanced Synthesis and Catalysis",

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T1 - A highly enantioselective catalytic domino aza-Michael/aldol reaction

T2 - One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines

AU - Sundén, Henrik

AU - Rios, Ramon

AU - Ibrahem, Ismail

AU - Zhao, Gui Ling

AU - Eriksson, Lars

AU - Córdova, Armando

PY - 2007/4

Y1 - 2007/4

N2 - 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.

AB - 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.

KW - Asymmetric catalysis

KW - Aza-Michael reaction

KW - Domino reactions

KW - Nitrogen heterocycles;α,βunsaturated aldehydes

UR - https://www.scopus.com/pages/publications/34250002963

U2 - 10.1002/adsc.200600513

DO - 10.1002/adsc.200600513

M3 - Article

AN - SCOPUS:34250002963

SN - 1615-4150

VL - 349

SP - 827

EP - 832

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

ER -

A highly enantioselective catalytic domino aza-Michael/aldol reaction: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines

Abstract

Keywords

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