Aminocarboxylic startg

Startg. 2,3-azetidinedione added to ca. 1.4 eqs. m-chloroperoxybenzoic acid in methylene chloride at — 20°, the mixture stirred for 60 min, treated dropwise with a soln. of / r/-butylamine and pyridine in the same solvent, and stirred at room temp, for 70 min product. Y 70%. F.e. and a-aminocarboxylic acid esters with alcohols, also 3-(a-nitroalkylidene)-2-azetidinones, s. F.P. Cossio et al., Tetrahedron Letters 29, 3133-6 (1988). 

A soln. of startg. chiral lactone in abs. ethanol treated with N-cyclohexylhydroxyl-amine at room temp, for 3 h, the solvent removed, the mixture chromatographed, and the adduct silylated by standard procedure - (3S)-product. Y 73%. The products are readily converted to chiral P-aminocarboxylic acids. F.e.s. I. Panfil et al.. Tetrahedron Letters 30, 1527-8 (1989). 

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