Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane
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).
Whitesell, James K.,Wong, Man-Shing
p. 597 - 601
(2007/10/02)
Improved Method for the Preparation of Enantiomerically Pure Sulfinate Esters
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Whitesell, James K.,Wong, Man-Shing
p. 4552 - 4554
(2007/10/02)
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