Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone

被引：111

作者：

Zhou, Lin ^{[1
]}

Lin, Lili ^{[1
]}

Ji, Jie ^{[1
]}

Xie, Mingsheng ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ALKYLATION; DIRECT CONJUGATE ADDITION; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; TERTIARY STEREOCENTERS; ADJACENT QUATERNARY; EFFICIENT SYNTHESIS; ALLYLIC ALKYLATION; HIGHLY EFFICIENT; NATURAL-PRODUCTS;

D O I：

10.1021/ol200939t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural a-angelica lactone has been successfully developed. It was demonstrated that the nonactivated natural a-angelica lactone Is a useful vinylogous nucleophile to give the chiral delta-amino gamma,gamma-disubstituted butenolide carbonyl derivatives. The N,N'-dioxide L2-Se-III complex is efficient toward tie obtention of a range of corresponding products with adjacent quaternary and tertiary stereocenters in excellent dr and ee values.

引用

页码：3056 / 3059

页数：4

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