Iridium-Catalyzed Regioselective and Enantioselective Allylation of Trimethylsiloxyfuran

被引：78

作者：

Chen, Wenyong ^{[1
]}

Hartwig, John F. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 37期

关键词：

MONOSUBSTITUTED ALLYLIC ACETATES; BAYLIS-HILLMAN ACETATES; ASYMMETRIC-SYNTHESIS; ALDOL REACTION; 2,4-DISUBSTITUTED CYCLOPENTENONES; GAMMA-BUTENOLIDES; NITRO-COMPOUNDS; SUBSTITUTION; ALKYLATION; CONSTRUCTION;

D O I：

10.1021/ja306850b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the regio- and enantioselective allylation of an ester enolate, trimethylsiloxyfuran. This enolate reacts at the 3-position with linear aromatic allylic carbonates or aliphatic allylic benzoates to form the branched substitution products in the presence of a metallacyclic iridium catalyst. This process provides access to synthetically important 3-substituted butenolides in enantioenriched form. Stoichiometric reactions of the allyliridium intermediate suggest that the trimethylsiloxyfuran is activated by the carboxylate leaving group.

引用

页码：15249 / 15252

页数：4

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