Stereocontrolled Synthesis of Acyclic Tri- and Tetra-C-Substituted α-Alkoxymethyl α,β-Unsaturated Esters

Dennis G. Hall; Daniel Chapdelaine; Patrice Préville; Pierre Deslongchamps

doi:10.1055/s-1994-22966

Synlett 1994; 1994(8): 660-662
DOI: 10.1055/s-1994-22966

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Stereocontrolled Synthesis of Acyclic Tri- and Tetra-C-Substituted α-Alkoxymethyl α,β-Unsaturated Esters

Dennis G. Hall^* , Daniel Chapdelaine, Patrice Préville, Pierre Deslongchamps

^*Laboratoire de synthèse organique, Département de chimie, Faculté des sciences, Université de Sherbrooke, Sherbrooke, Québec J1K 2R1, Canada

Abstract

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α-Haloethers were found to efficiently trap vinylcopper intermediates derived from homocuprate conjugate addition on acetylenic esters. This tandem bifunctionalization affords good to high yields of tri- and tetra-C-substituted α-alkoxymethyl α,β-unsaturated esters with high cis-addition stereoselectivity.

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