Enantiopure sulforaphane analogues with various substituents at the sulfinyl sulfur: Asymmetric synthesis and biological activities
(Chemical Equation Presented) A convergent and high-yielding approach for the asymmetric synthesis of sulforaphane 2 and four analogues differently substituted at the sulfinyl sulfur has been developed. The key step of the synthesis is the diastereoselect
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)
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