ChemInform Abstract: Preparation and Ring‐Opening Reactions of N‐Diphenylphosphinyl Vinyl Aziridines.

Abstract

Preparation and Ring-Opening Reactions of N-Diphenylphosphinyl Vinyl Aziridines. -LDA-Lithiation of allyl bromide (I) followed by ZnCl2 generates α -bromo allyllithium which reacts with phosphinyl aldimines to form mainly trans-or cis-aziridines depending on the substituent R. The arylated trans-derivatives (cf. (IIIa)) react with a variety of carbon nucleophiles to yield selectively or exclusively the C-3 attack products. Chalcogen nucleophiles such as (XI) give mainly the C-2 ring opened product (cf. (XIII)). - (CANTRILL, A. A.; JARVIS, A. N.; OSBORN, H. M. I.; OUADI, A.; SWEENEY, J. B.; Synlett (1996) 9, 847-849; Dep. Chem., Univ. Reading, Reading RG6 6AD, UK; EN)