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手性亚砜的对映选择性磺化反应。

Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis.

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).

出版信息

Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12354-8. doi: 10.1002/anie.201305023. Epub 2013 Oct 2.

DOI:10.1002/anie.201305023
PMID:24115649
Abstract

Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.

摘要

众人拾柴火焰高

在烯酮的有机催化不对称磺化反应中,亚磺酰亚胺通过 N-杂环卡宾(NHC)催化剂的活化,释放出亚磺酸阴离子,该阴离子对烯酮进行亲核加成。该过程的对映选择性通过手性硫脲/胺共催化剂通过阴离子识别和氢键相互作用进行控制。Tol=p-甲苯基。

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