Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System

Youn, So Won; Song, Hyoung Sub; Park, Jong Hyub

doi:10.1021/ol5000617

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Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System

Youn, So Won;
Song, Hyoung Sub;
Park, Jong Hyub

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WEB OF SCIENCE

65

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SCOPUS

64

초록

It is demonstrated that two organocatalysts, achiral NHC and chiral bifunctional cinchonine, are mutually compatible and operating concurrently and effectively to promote the asymmetric domino oxidation/oxa-Michael addition reaction. This protocol allowed access to both enantiomers of a product by using two natural, inexpensive pseudoenantiomeric cinchona alkaloids, cinchonine and cinchonidine, as well as to phthalides containing a chiral quaternary carbon center in good enantioselectivities.

키워드

N-HETEROCYCLIC CARBENE; CATALYTIC KINETIC RESOLUTION; ENANTIOSELECTIVE SYNTHESIS; AROMATIC-ALDEHYDES; CASCADE CATALYSIS; NHC; CONSTRUCTION; PROTONATION; OXIDATION; CO2

제목: Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System

저자: Youn, So Won; Song, Hyoung Sub; Park, Jong Hyub

DOI: 10.1021/ol5000617

발행일: 2014-02

유형: Article

저널명: Organic Letters

권: 16

호: 3

페이지: 1028 ~ 1031