Journal of Organic Chemistry p. 597 - 601 (1994)
Update date:2022-08-17
Topics:
Whitesell, James K.
Wong, Man-Shing
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 10:1 to 96:4 under conditions affording high chemical yields.The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).
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