An asymmetric route to novel chiral cyclohexenones with spiro-connected cyclopentenes. Further utility of chiral bicyclic thiolactams and the [3,3] thio-Claisen products

被引：29

作者：

Lemieux, RM ^{[1
]}

Devine, PN ^{[1
]}

Mechelke, MF ^{[1
]}

Meyers, AI ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 10期

关键词：

D O I：

10.1021/jo982426q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sequential allylation of chiral, nonracemic thiolactam 8 affords clean thio-Claisen [3,3] products ii. The stereoselectivity of the rearrangement was found to be on the order of 10-11:1, with the exo-endo products responsible for the mixture. Addition of hydride or methyllithium-cerium chloride gave clean addition to the thiolactam in the form of its iminium salts 12. Hydrolysis gave 4,4-dialkylcyclohexenones 16, which were cyclized to the cyclopentene derivatives 16 using Grubbs' catalyst.

引用

页码：3585 / 3591

页数：7

共 16 条

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