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Alkynyl Group as Activating Group: Base‐Catalyzed Diastereoselective Domino Reactions of Electron‐Deficient Enynes
Author(s) -
Li Wenbo,
Xiao Yuanjing,
Zhang Junliang
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900633
Subject(s) - chemistry , domino , cyclopentanes , enyne , catalysis , group (periodic table) , base (topology) , stereoselectivity , cascade reaction , medicinal chemistry , leaving group , malonate , organic chemistry , mathematical analysis , mathematics
This paper describes a base‐catalyzed domino reaction of electron‐deficient enynes with malonate‐derived α,β‐unsaturated esters and ketones, which provides a rapid, stereoselective access to multi‐functionalized cyclopentanes and inden‐5(6 H )‐ones in high yields. In this reaction, the alkynyl group of the enyne acts as an activating group rather than a reacting group.