The Journal of organic chemistry

Tandem Blaise/retro-Blaise reaction for the nitrile-mediated regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1- …

JH Kim, YS Chun, S Lee

Index: Kim, Ju Hyun; Chun, Yu Sung; Lee, Sang-Gi Journal of Organic Chemistry, 2013 , vol. 78, # 22 p. 11483 - 11493

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Citation Number: 13

Abstract

We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1- alkynes and 1, 3-enynes. This reaction is made possible by a reversible addition of enolates to a nitrile (Blaise reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1, 3-enynes. Subsequent removal of the nitrile ...