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ChemInform Abstract: Synthesis of Enantiomerically Pure Vinylcyclopropanes by SN2′ Allylic Carboxylate Displacements.

✍ Scribed by Stephen F. Martin; Roy K. Hom; Michael P. Dwyer

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Enantiomerically Pure Vinylcyclopropanes by S N 2' Allylic Carboxylate Displacements. -The readily available optically pure lactones (I) or (XIII) undergo palladium-catalyzed displacement by a variety of stabilized carbon, oxygen, and nitrogen nucleophiles to afford as major S N 2' products enantiomerically pure vinyl cyclopropanes and in trace amounts S N 2 products (allyl cyclopropanes). The vinyl cyclopropanes are formed exclusively or predominantly as E-isomers. Lower and higher order cyanocuprates also react with these lactones to give products of S N 2' opening of the lactone moiety. -(MARTIN,

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