Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones

被引：50

作者：

Hao, Xiaoyu ^{[1
]}

Liu, Xiaohua ^{[1
]}

Li, Wei ^{[1
]}

Tan, Fei ^{[1
]}

Chu, Yangyang ^{[1
]}

Zhao, Xiaohu ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 01期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; CARBON QUATERNARY STEREOCENTERS; N-HETEROCYCLIC CARBENES; AROMATIC-ALDEHYDES; ALPHA-DIAZOESTERS; BUILDING-BLOCKS; NATURAL-PRODUCT; ONE-POT; CONSTRUCTION; DERIVATIVES;

D O I：

10.1021/ol4031217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.

引用

页码：134 / 137

页数：4

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