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Synlett 2001; 2001(12): 1855-1858
DOI: 10.1055/s-2001-18754
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Asymmetric Protonation of Lithium Enolate of α-Amino Acid Derivatives using Chiral Brønsted Acids

Akira Yanagisawa* , Yoshihiro Matsuzaki, Hisashi Yamamoto
  • *Department of Chemistry, Faculty of Science, Chiba University, Inage, Chiba 263-8522, Japan; Fax: + 81 (52) 7893222; E-mail: yamamoto@cc.nagoya-u.ac.jp
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Publication Date:
04 December 2001 (online)

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Chiral alcohols possessing an asymmetric 2-oxazoline ring were synthesized as new chiral Brønsted acids from tetrahydro-2-furoic acid and (1S,2R)-2-amino-1,2-diphenylethanol. These alcohols were superior to (S,S)- or (R,R)-imide reported previously as a chiral proton source for enantioselective protonation of lithium enolate of an alanine derivative.

enantioselective protonation - lithium enolate - α-amino acid derivative - chiral alcohols - 2-oxazoline - asymmetric catalysis