铼催化的β-酮砜通过碳-碳键断裂实现末端炔烃的两个碳单元的区域和立体选择性加成。

Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones.

机构信息

Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Kita-ku, Okayama, Japan.

出版信息

Org Lett. 2011 Jun 3;13(11):2959-61. doi: 10.1021/ol2008507. Epub 2011 May 9.

DOI:10.1021/ol2008507

PMID:21553820

Abstract

Treatment of β-keto sulfones with terminal alkynes gave unsaturated δ-keto sulfones in good to excellent yields under rhenium catalysis. In this reaction, the insertion of the alkynes into the nonstrained carbon-carbon single bond between the α- and β-positions of the β-keto sulfones proceeded smoothly, and (Z)-isomers were produced with high regio- and stereoselectivities.

摘要

在铼催化下，β-酮亚砜与末端炔烃反应生成了不饱和的δ-酮亚砜，产率良好到优秀。在这个反应中，炔烃插入了β-酮亚砜的α-和β-位之间的非张力碳-碳单键，反应进行得很顺利，并且以高区域和立体选择性生成了（Z）异构体。