Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland-Claisen Rearrangement

被引：24

作者：

Crimmins, Michael T. ^{[1
]}

Knight, John D. ^{[1
]}

Williams, Philip S. ^{[1
]}

Zhang, Yan ^{[1
]}

机构：

[1] Univ N Carolina, Kenan Caudill Murray & Venable Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 09期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; BRIARANE-TYPE DITERPENOIDS; BETA-HYDROXY ESTERS;

D O I：

10.1021/ol5008422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A dianionic Ireland-Claisen rearrangement of chiral, nonracemic alpha-methyl-beta-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.

引用

页码：2458 / 2461

页数：4

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