Highly Enantioselective Copper-Catalyzed Alkylation of β-Ketoesters and Subsequent Cyclization to Spirolactones/Bi-spirolactones

被引：66

作者：

Deng, Qing-Hai ^{[1
]}

Wadepohl, Hubert ^{[1
]}

Gade, Lutz H. ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Anorgan Chem, D-69120 Heidelberg, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 06期

关键词：

ASYMMETRIC ALLYLIC ALKYLATION; CARBON QUATERNARY STEREOCENTERS; PHASE-TRANSFER CATALYSIS; KETO-ESTERS; STEREOGENIC CENTERS; AMMONIUM-SALTS; PINCER LIGANDS; ALCOHOLS; CONSTRUCTION; ALLYLATION;

D O I：

10.1021/ja211859w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cu-catalyzed enantioselective alkylation of beta-ketoesters using alcohols for in situ preparation of alkylating reagents is reported. A number of functionalized beta-ketoesters containing a quaternary carbon stereocenter are obtained with up to 99% ee. The alkylation products derived from 2-substituted allylic alcohols or their corresponding iodides can then be converted to spirolactones, bi-spirolactones, and related chiral target products.

引用

页码：2946 / 2949

页数：4

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