Catalytic Enantioselective Synthesis of Sulfinate Esters through the Dynamic Resolution of tert-Butanesulfinyl Chloride

Catalytic Enantioselective Synthesis of Sulfinate Esters through the Dynamic Resolution of tert-Butanesulfinyl Chloride

Development of a new synthetic route to obtain enantiomerically enriched tert-butanesulfinate esters in excellent yields through catalytic enantioselective sulfinyl transfer is described. As little as 0.5 mol % of chiral amine catalysts was used to couple racemic tert-butanesulfinyl chloride with ar...

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Veröffentlicht in:Journal of the American Chemical Society 2004-07, Vol.126 (26), p.8134-8135
Hauptverfasser: Evans, Jared W, Fierman, Matthew B, Miller, Scott J, Ellman, Jonathan A
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Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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container_end_page 8135
container_issue 26
container_start_page 8134
container_title Journal of the American Chemical Society
container_volume 126
creator Evans, Jared W
Fierman, Matthew B
Miller, Scott J
Ellman, Jonathan A
description Development of a new synthetic route to obtain enantiomerically enriched tert-butanesulfinate esters in excellent yields through catalytic enantioselective sulfinyl transfer is described. As little as 0.5 mol % of chiral amine catalysts was used to couple racemic tert-butanesulfinyl chloride with arylmethyl alcohols to provide sulfinate esters in near quantitative yields and with enantiomeric excesses up to 81%. The method represents the first example of the catalytic dynamic resolution of sulfinyl derivatives.
doi_str_mv 10.1021/ja047845l
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subjects Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
title Catalytic Enantioselective Synthesis of Sulfinate Esters through the Dynamic Resolution of tert-Butanesulfinyl Chloride
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