We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Highly Enantioselective Synthesis of Fused Tri‐ and Tetrasubstituted Aziridines: aza‐Darzens Reaction of Cyclic Imines with α‐Halogenated Ketones Catalyzed by Bifunctional Phosphonium Salt.
- Authors
Pan, Jianke; Wu, Jia‐Hong; Zhang, Hongkui; Ren, Xiaoyu; Tan, Jian‐Ping; Zhu, Lixiang; Zhang, Hong‐Su; Jiang, Chunhui; Wang, Tianli
- Abstract
The first enantioselective aza‐Darzens reaction of cyclic imines with α‐halogenated ketones was realized under mild reaction conditions by using amino‐acid‐derived bifunctional phosphonium salts as phase‐transfer promoters. A variety of structurally dense tri‐ and tetrasubstituted aziridine derivatives, containing benzofused heterocycles as well as spiro‐structures, were readily synthesized in high yields with excellent diastereo‐ and enantioselectivities (up to >20:1 d.r. and >99.9 % ee). The highly functionalized aziridine products could be easily transformed into different classes of biologically active compounds.
- Subjects
AZIRIDINES; DARZENS reaction; IMINES; PHOSPHONIUM compounds; KETONES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 22, p7503
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201900613