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Chiral Induction in Originally Racemic Amino Acids via 5‐Acyl and 5‐Acyloxyaminooxazoles
Author(s) -
Lipshutz Bruce H.,
Hungate Randall W.,
Mccarthy Keith E.
Publication year - 1986
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198600009
Subject(s) - chemistry , nitrile , dipeptide , asymmetric induction , chirality (physics) , amide , ring (chemistry) , stereochemistry , amino acid , sequence (biology) , organic chemistry , enantioselective synthesis , catalysis , biochemistry , chiral symmetry , physics , quark , quantum mechanics , nambu–jona lasinio model
A variety of chiral 2,4‐disubstituted‐5‐trifluoroacetamido‐,5‐carbobenzyloxyamino, and 5‐β,β,β,‐trichloroethoxycarbonylaminooxazoles have been prepared from diamide, dipeptide, or amide nitrile precursors. Conversion to their (poly)amide equivalents via a deacylation/hydration sequence is described. The extent of induction of chirality realized upon ring opening in each case is determined by HPLC.