N-酰基氮丙啶的对映选择性合成和立体选择性开环。
Enantioselective synthesis and stereoselective ring opening of N-acylaziridines.
机构信息
Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, NC 28403, USA.
出版信息
Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9842-5. doi: 10.1002/anie.201204224. Epub 2012 Sep 3.
PMID:22945340
Abstract
Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL.
摘要
通过亲核开环反应实现了 N-酰基氮丙啶的动力学拆分，反应在硼催化条件下使用（R）-BINOL 作为手性修饰剂（见方案；Ar=3,5-二硝基苯基）。消耗的氮丙啶对映异构体可以进一步转化为手性富集的 1,2-氯酰胺，并回收（R）-BINOL。
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