Asymmetric Conjugate Addition of Grignard Reagents to Pyranones

被引：31

作者：

Mao, Bin ^{[1
]}

Fananas-Mastral, Martin ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 02期

关键词：

DIELS-ALDER REACTIONS; PHOSPHINE-PHOSPHITE LIGANDS; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; NATURAL-PRODUCTS; 2H-PYRAN-2-ONE; 1,4-ADDITION; 2-PYRONES; 3,4-DIHYDROPYRAN-2-ONES; SECOLOGANIN;

D O I：

10.1021/ol303141x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as beta-alkyl substituted aldehydes or beta-bromo-gamma-alkyl substituted alcohols with excellent regio- and stereoselectivity.

引用

页码：286 / 289

页数：4

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