4.4 Article

A study of conjugate addition to a γδ-dioxolanyl-α,β-unsaturated ester

Journal

TETRAHEDRON LETTERS
Volume 42, Issue 26, Pages 4281-4283

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)00719-5

Keywords

conjugate addition; difficult reactions; copper reagents; copper(I) bromide dimethylsulfide complex; copper(I) cyanide (CuCN); trimethylsilyl chloride (TMSCl); alpha,beta-unsaturated substrates with oxygen substitution at gamma,beta-positions

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Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts. (C) 2001 Elsevier Science Ltd. All rights reserved.

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