碘化钐促进的叶立德-丙二烯环化反应。

Ketyl-allene cyclizations promoted by samarium(II) iodide.

作者信息

Molander Gary A, Cormier Elizabeth Pollina

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

J Org Chem. 2005 Apr 1;70(7):2622-6. doi: 10.1021/jo047887s.

DOI:10.1021/jo047887s

PMID:15787552

Abstract

[reaction: see text] Samarium(II) iodide has proven to be an effective reagent for intramolecular reductive coupling reactions. Previous investigations of intramolecular ketyl-olefin coupling reactions provided carbocycles in excellent yield and good diastereoselectivity. This method has been extended to ketyl cyclizations with allenes. Substrates leading to both carbocycles and heterocycles in a selective manner are explored.

摘要

[反应：见正文] 碘化钐（II）已被证明是分子内还原偶联反应的有效试剂。先前对分子内酮基-烯烃偶联反应的研究以优异的产率和良好的非对映选择性提供了碳环。该方法已扩展到与丙二烯的酮基环化反应。探索了以选择性方式生成碳环和杂环的底物。