Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids

…, TD Churkina, NS Ikonnikov, AA Chesnokov…

Index: Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan Russian Chemical Bulletin, 1999 , vol. 48, # 5 p. 917 - 923

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Citation Number: 12

Abstract

Abstract It is shown that sodium alkoxides formed from (4 R, 5 R)-2, 2-dimethyl-1, 3- dioxolane-4, 5-bis (diphenylmethanol)((R, R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α- methylphenyl-alanine,(R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61–93% ...