Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl 2 . These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity. 852

The aza-Darzens reaction of the chiral enolate derived from bromoacetylcamphorsultam 1 with N-(diphenyl-phosphiny1)aryl-and tert-butyl-methanimines proceeds in good yield to give cis-N-(diphenylphosphiny1)aziridinylcar-bony1 sultams with high de. Monochiral cis-aziridinecarboxylates may be obtained in acceptable yield by hydrolysis of these sultams.

SummaryPredominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

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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)