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Paper | Regular issue | Vol 78, No. 2, 2009, pp.471-485
Published online, 9th October, 2008
DOI: 10.3987/COM-08-11537
■ Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols

Kimio Higashiyama,* Masataka Matsumura, Hiroshi Kojima, and Takayasu Yamauchi

*Institute of Medicinal Chemistry; Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded β-amino alcohols with an (S)-chiral center at the β position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave β-amino alcohols that have an (S)-chiral center at the α position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the β-amino alcohols with an (R)-chiral center at the α position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).