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Synlett 2010(14): 2097-2100  
DOI: 10.1055/s-0030-1258520
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of α-Benzylalanine Using trans-3,4-Dihydro-3,4-diaryldibenzo[c,g]phenanthrene-3,4-diols

Mitsuru Kitamura*, Daisuke Kitahara, Tatsuo Okauchi
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu-shi, Fukuoka, 804-8550 Japan
Fax: +81(93)8843304; e-Mail: kita@che.kyutech.ac.jp;
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Publication History

Received 27 May 2010
Publication Date:
22 July 2010 (online)

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Abstract

Asymmetric benzylation of a benzophenone Schiff’s base of alanine ethyl ester was successfully conducted using trans-3,4-dihydro-3,4-diaryldibenzo[c,g]phenanthrene-3,4-diol as a chiral source.

Key words

amino acids - asymmetric synthesis - biaryls - diols - phase-transfer catalysis

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12

In an initial screening on bases (NaH, KH, CaH2, NaOH, KOH, CsOH˙H2O, CsCO3, t-BuONa, t-BuOK), t-BuOK was good in terms of the yield and/or ee of the alkylated product 4.