CHEMISTRY OF AZIRIDINE CARBOXYLIC-ACIDS . 5. ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE AZIRIDINE CARBOXYLIC-ACID DERIVATIVES FROM (R)-GLYCERALDEHYDE AND (S)-GLYCERALDEHYDE ACETONIDE

The alpha-bromoacrylic acid derivatives 2 reacted with benzylamine by ring closure to cis-aziridines 3 and trans-aziridines 4 with greater t han or equal to 99% diastereomeric excess. The aziridines 3 and 4 were hydrogenated by LiAlH4 to give alcohols 5 and 6. Tosylations of 6 yie lded the crystalline sulfonamides 7. The absolute configurations of (2 R,3S,4R)-3c, (2S,3R,4S)-5 and (1R,2R, 4R)-7 were determined by X-ray a nalyses.