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
收藏
页码：2458 / 2461
页数：4
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