Chiral BrOnsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters

被引：22
|
作者：
Bew, Sean P. [1 ]
Liddle, John [2 ]
Hughes, David L. [1 ]
Pesce, Paolo [1 ]
Thurston, Sean M. [1 ]
机构：
[1] Univ East Anglia, Sch Chem, Norwich Res Pk, Norwich NR4 7TJ, Norfolk, England
[2] GlaxoSmithKline, Dept Med Chem, Gunnels Wood Rd, Stevenage, Herts, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 19期
基金：
英国工程与自然科学研究理事会;
关键词：
asymmetric catalysis; aziridine; BrOnsted acids; multicomponent reactions; MANNICH-TYPE REACTION; DIELS-ALDER REACTION; BOC-IMINES; ORGANOCATALYSIS; DESIGN; ALKYL;
D O I：
10.1002/anie.201611990
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a multi-component asymmetric BrOnsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61-98%) and mostly >90% optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.
引用
收藏
页码：5322 / 5326
页数：5
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