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Asymmetric synthesis of β‐amino acids and α‐deuterated β‐amino acids via conjugate addition of homochiral amidocuprates
Author(s) -
Sewald Norbert,
Hiller Klaus D.,
Helmreich Brigitte
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199505133
Subject(s) - chemistry , conjugate , amino acid , stereoselectivity , amine gas treating , deuterium , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , biochemistry , mathematical analysis , physics , mathematics , quantum mechanics
Conjugate addition of homochiral amidocuprates based on N ‐[( R )‐1‐phenylethyl]trimethylsilylamine or bis[( R )‐1‐phenylethyl]amine to α,β‐unsaturated esters provides an efficient methodology for the asymmetric synthesis of β‐amino acids. Trapping of the intermediate enolate with D 2 O yields α‐deuterated β‐amino acids with excellent stereoselectivity.