Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

James K. Whitesell; Man Shing Wong

doi:10.1021/jo00082a016

Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

James K. Whitesell^*, Man Shing Wong

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

68 Citations (Scopus)

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 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).

Original language	English
Pages (from-to)	597-601
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	59
Issue number	3
DOIs	https://doi.org/10.1021/jo00082a016
Publication status	Published - 1 Feb 1994

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Organic Chemistry

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title = "Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane",

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 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).",

author = "Whitesell, {James K.} and Wong, {Man Shing}",

note = "Financial support of this research by the National Institutes of Health (GM-31750), the Robert A. Welch Foundation (F-626), and the National Science Foundation (DMR-9014026) as well as a generous gift of (+)-(1S,2R)-2-phenylcyclohexanol from Hofmann LaRoche, Nutley, NJ are gratefully acknowledged. ",

year = "1994",

month = feb,

day = "1",

doi = "10.1021/jo00082a016",

language = "English",

volume = "59",

pages = "597--601",

journal = "Journal of Organic Chemistry",

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T1 - Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

AU - Whitesell, James K.

AU - Wong, Man Shing

N1 - Financial support of this research by the National Institutes of Health (GM-31750), the Robert A. Welch Foundation (F-626), and the National Science Foundation (DMR-9014026) as well as a generous gift of (+)-(1S,2R)-2-phenylcyclohexanol from Hofmann LaRoche, Nutley, NJ are gratefully acknowledged.

PY - 1994/2/1

Y1 - 1994/2/1

N2 - 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).

AB - 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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U2 - 10.1021/jo00082a016

DO - 10.1021/jo00082a016

M3 - Journal article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

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