High diastereofacial selectivity in the reaction of silyl enol ethers with chlorosulfides

Iqbal, Javed ; Shukla, Alka (1991) High diastereofacial selectivity in the reaction of silyl enol ethers with chlorosulfides Tetrahedron, 47 (41). pp. 8753-8766. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)96197-6

Abstract

The chlorosulfides 1 or 2 react with silyl enol ethers in presence of anhydrous zinc bromide to give mainly the corresponding syn products 4 or 6 respectively. The high syn selectivity of these reaction is explained by nucleophilic addition to a Chelated Chiral thioniun ion.

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