Invertible Enantioselectivity in 6′-Deoxy-6′-acylamino-β-isocupreidine-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction: Key Role of Achiral Additive

被引：63

作者：

Abermil, Nacim ^{[1
]}

Masson, Geraldine ^{[1
]}

Zhu, Jeping ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

关键词：

N-SULFONATED IMINES; METHYL VINYL KETONE; LEWIS-BASE ORGANOCATALYST; ISOCUPREIDINE BETA-ICD; DUAL CATALYST CONTROL; BRONSTED ACID; BIFUNCTIONAL ORGANOCATALYSTS; ACTIVATED OLEFINS; ALDOL ADDITIONS; CHIRAL SOURCE;

D O I：

10.1021/ol901920s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-ICD (1a) or beta-ICD-amide(1e)-catalyzed aza-Morita-Baylis-Hillman reaction between N-sulfonylimines 3 and alkyl vinyl ketones 4 produced the (R)-enriched adducts 5. By adding a catalytic amount beta-naphthol (2a), the enantioselectivity of the same reaction was inversed leading to (S)-5 in excellent yields and enantioselectivities. Both aromatic and aliphatic imines are accepted as substrates for this reaction.

引用

页码：4648 / 4651

页数：4

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