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

页码：5322 / 5326

页数：5

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