Premium
Asymmetric syntheses via heterocyclic intermediates, XXXI. Asymmetric synthesis of various non‐proteinogenic amino acid methyl esters (functionalized in the carbon chain) and amino acids by the bislactim ether method
Author(s) -
Schöllkopf Ulrich,
Busse Ulrich,
Lonsky Ralph,
Hinrichs Rolf
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619861209
Subject(s) - chemistry , hydrolysis , alkylation , amino acid , ether , yield (engineering) , organic chemistry , side chain , carbon fibers , catalysis , biochemistry , materials science , polymer , metallurgy , composite number , composite material
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.