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Paper | Special issue | Vol 42, No. 2, 1996, pp.701-722
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S76
Ring Opening of Optically Active cis-Disubstituted Aziridino Alcohols: An Enantiodivergent Synthesis of Functionalized Amino Alcohol Derivatives

Kaoru Fuji, Takeo Kawabata, Yoshimitsu Kiryu, and Yukio Sugiura

*Institute for Chemistry, Kyoto University, Uji, Kyoto 611-0011, Japan


Ring-opening reactions of optically active cis-disuhstituted aziridino alcohols have been investigated. Regio- and stereo-selective ring opening took place with internal and external nucleophiles. Unusual amino acids derivatives (14) and (15), the key synthetic intermediates for bestatin and related peptides, have been prepared.