A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides

被引：46

作者：

Aubert, Sidonie ^{[1
]}

Katsina, Tania ^{[1
]}

Arseniyadis, Stellios ^{[1
]}

机构：

[1] Queen Mary Univ London, Sch Biol & Chem Sci, Mile End Rd, London E1 4NS, England

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

关键词：

ASYMMETRIC ALLYLIC ALKYLATION; VINYLOGOUS MANNICH REACTIONS; BAYLIS-HILLMAN ACETATES; GAMMA-BUTENOLIDES; ALDOL REACTION; ENANTIOSELECTIVE CONSTRUCTION; SUBSTITUTION-REACTIONS; EFFICIENT; BUTYROLACTONES; METHODOLOGIES;

D O I：

10.1021/acs.orglett.9b00521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and highly enantio- (up to 94:6 er) and diastereoselective (up to >20:1 dr) synthesis of gamma-butenolides bearing two adjacent stereogenic centers is reported featuring a sequential direct palladium-catalyzed asymmetric allylic alkylation/(E)-selective cross-metathesis/[3,3]-sigmatropic Cope rearrangement from readily available alpha-substituted (5H)-furan-2-ones.

引用

页码：2231 / 2235

页数：5

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