通过叔丁基亚磺酰氯的动态拆分实现亚磺酸酯的催化对映选择性合成。

Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride.

作者信息

Evans Jared W, Fierman Matthew B, Miller Scott J, Ellman Jonathan A

机构信息

Center for New Directions in Organic Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.

出版信息

J Am Chem Soc. 2004 Jul 7;126(26):8134-5. doi: 10.1021/ja047845l.

DOI:10.1021/ja047845l

PMID:15225052

Abstract

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.

摘要

本文描述了一种新的合成路线，通过催化对映选择性亚磺酰基转移，以优异的产率获得对映体富集的叔丁基亚磺酸酯。使用低至0.5 mol%的手性胺催化剂，将外消旋叔丁基亚磺酰氯与芳基甲醇偶联，以接近定量的产率和高达81%的对映体过量提供亚磺酸酯。该方法代表了亚磺酰基衍生物催化动态拆分的首个实例。