通过内消旋氮丙啶的有机催化去对称化实现β-氨基苯硫醚的高度对映选择性合成。
Highly enantioselective synthesis of beta-amidophenylthioethers by organocatalytic desymmetrization of meso-aziridines.
作者信息
Della Sala Giorgio, Lattanzi Alessandra
机构信息
Department of Chemistry, University of Salerno, Via Ponte Don Melillo 8, 84024 Fisciano (SA), Italy.
出版信息
Org Lett. 2009 Aug 6;11(15):3330-3. doi: 10.1021/ol901209n.
PMID:19585986
Abstract
The desymmetrization of N-acylaziridines with Me(3)SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.
摘要
在市售的（R）-和（S）-VAPOL磷酸催化下，用三甲基硅基苯硫醚（Me(3)SiSPh）对N-酰基氮杂环丙烷进行去对称化反应，以高度对映选择性和高效的方式（对映体过量78 - 99%）生成β-（N-酰基氨基）苯硫醚。选择合适的氮杂环丙烷/亲核试剂/催化剂摩尔比对于获得高对映体过量至关重要。
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