A Direct Route to C-Vinylaziridines: Reaction of N-Sufonylimines with Allylic Ylides under Phase-Transfer Conditions or with Preformed Ylides at Low Temperature

An-Hu Li; Li-Xin Dai; Xue-Long Hou; Min-Bo Chen

doi:10.1021/jo952245d

A Direct Route to C-Vinylaziridines: Reaction of N-Sufonylimines with Allylic Ylides under Phase-Transfer Conditions or with Preformed Ylides at Low Temperature

J Org Chem. 1996 Jul 12;61(14):4641-4648. doi: 10.1021/jo952245d.

Authors

An-Hu Li¹, Li-Xin Dai, Xue-Long Hou, Min-Bo Chen

Affiliation

¹ Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, and Laboratory of Computer Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 11667392
DOI: 10.1021/jo952245d

Abstract

Allylic sulfonium salts 3, 5, 7, 11, 12, 13, and arsonium salt 14 react with aromatic, heteroaromatic, and alpha,beta-unsaturated N-sulfonylimines under solid-liquid phase-transfer conditions in the presence of KOH at room temperature to produce, respectively, vinyl-, (beta-phenylvinyl)-, and [beta-(trimethylsilyl)vinyl]aziridines in excellent yields within several minutes. In some cases, pyrroline compound 9 is obtained as a minor product. This aziridination reaction has also been carried out with preformed ylides, generated from sulfonium salts 3, 7, arsonium salt 14, and telluronium salts 15, 16 with a base in THF at -78 degrees C. In most examples, quantitative yields were achieved. However, the trans/cis selectivity of the reaction was not high in either case. A semistable allylic sulfonium ylide, i.e., dimethylsulfonium 3-(trimethylsilyl)allylide, was found to not undergo an expected [2,3]-sigma-rearrangement and so can also be used in this reaction.