The Journal of Organic Chemistry

Asymmetric synthesis of chiral sulfinate esters and sulfoxides. Synthesis of sulforaphane

JK Whitesell, MS Wong

Index: Whitesell, James K.; Wong, Man-Shing Journal of Organic Chemistry, 1994 , vol. 59, # 3 p. 597 - 601

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Citation Number: 65

Abstract

Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6). Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, Et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 1 0 1 to 96: 4 under ...