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Highly Enantioselective Synthesis of Fused Tri‐ and Tetrasubstituted Aziridines: aza‐Darzens Reaction of Cyclic Imines with α‐Halogenated Ketones Catalyzed by Bifunctional Phosphonium Salt
Author(s) -
Pan Jianke,
Wu JiaHong,
Zhang Hongkui,
Ren Xiaoyu,
Tan JianPing,
Zhu Lixiang,
Zhang HongSu,
Jiang Chunhui,
Wang Tianli
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900613
Subject(s) - enantioselective synthesis , phosphonium , bifunctional , aziridine , chemistry , phosphonium salt , catalysis , organic chemistry , salt (chemistry) , combinatorial chemistry , ring (chemistry)
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.