Asymmetric syntheses via heterocyclic intermediates, XXXI. Asymmetric synthesis of various non??proteinogenic amino acid methyl esters (functionalized in the carbon …

U Schoellkopf, U Busse, R Lonsky…

Index: Schoellkopf, Ulrich; Busse, Ulrich; Lonsky, Ralph; Hinrichs, Rolf Liebigs Annalen der Chemie, 1986 , # 12 p. 2150 - 2163

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Citation Number: 15

Abstract

Abstract The lithiated bislactim ethers 5, 10, 12, and 23 were alkylated with a variety of alkylating agents 6 to give the alkylated bislactim ethers 7, 11, 13, and 24 with a high degree of asymmetric induction (up to 99%). Upon hydrolysis these furnished the optically active amino acid methyl esters of type 8, 14, or 25. Some of these amino acid esters were further hydrolyzed to yield the amino acids.