Stereoselective nucleophilic addition with a new chiral template and its application to the synthesis of optically active α-arylglycine derivatives

S Tohma, K Rikimaru, A Endo, K Shimamoto, T Kan…

Index: Tohma, Shigemitsu; Rikimaru, Kentaro; Endo, Atsushi; Shimamoto, Keiko; Kan, Toshiyuki; Fukuyama, Tohru Synthesis, 2004 , # 6 p. 909 - 917

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Citation Number: 12

Abstract

Abstract 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, arylboronic acids and other nucleophiles. Additionally, several Lewis acid- promoted addition reactions with iminolactone 4 were accomplished efficiently. These ...