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Synlett 2001; 2001(7): 1179-1181
DOI: 10.1055/s-2001-15168
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Synthesis of Optically Active α-Arylglycines: Stereoselective Mannich-Type Reaction with a New Chiral Template

Shigemitsu Tohma* , Atsushi Endo, Toshiyuki Kan, Tohru Fukuyama
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, The Japan Science and Technology Corporation (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax + 81-3-58 02-86 94; E-mail: fukuyama@mol.f.u-tokyo.ac.jp
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Publication History

Publication Date:
31 December 2001 (online)

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Mannich-type reaction of phenols with iminolactone 4, readily prepared from commercially available phenylglycine, proceeded with high stereoselectivity to give α-arylglycine derivatives. The reaction was also applicable to other electron-rich aromatic compounds and aryl boronic acids. These adducts could be readily converted to the corresponding optically active α-arylglycines.

α-arylglycines - Mannich-type reaction - iminolactone - phenol - arylboronic acid