Regio- and stereoselectivity in reactions of 2,3-cis- and trans-3-alkyl-2-vinylaziridines with organocopper reagents: Importance of 2,3-cis-stereochemistry in controlling selectivity

✍ Scribed by Hiroshi Aoyama; Norio Mimura; Hiroaki Ohno; Kiyonori Ishii; Ayako Toda; Hirokazu Tamamura; Akira Otaka; Nobutaka Fujii; Toshiro Ibuka

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 253 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01726-7

✦ Synopsis

By treatment with organocopper reagents, N-activated 2,3-cis-3-alkyl-2-vinylaziridines produced exclusively (E)-allyl amines in high yields, presumably via an anti-SN2' reaction pathway. On the other hand, under otherwise identical conditions, N-activated 2,3-trans-3-alkyl-2-vinylazaridines gave an 85-96: ! 5-4 mixture of (E)-and (Z)-allyl amines. In reactions of certain N-activated 2,3-trans-3alkyl-2-vinylaziridines, SN2 reaction products were obtained in only 2-3% yield.