Tetrahedron

Scope of the chromium (II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu 3 SnCHBr 2

DM Hodgson, LT Boulton, GN Maw

Index: Hodgson, David M.; Boulton, Lee T.; Maw, Graham N. Tetrahedron, 1995 , vol. 51, # 12 p. 3713 - 3724

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Citation Number: 37

Abstract

The synthesis of E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described. A mechanism is proposed to account for the alkene geometry in chromium (II)-mediated alkene synthesis which involves stereoselective addition by a gem- dichromium reagent to an aldehyde followed by a stereospecific elimination step.