Double asymmetric induction as a mechanistic probe: conjugate addition for the asymmetric synthesis of a pseudotripeptide.
Double asymmetric induction as a mechanistic probe indicates that, for the conjugate addition of (R)- and (S)-lithium N-benzyl-N--alpha-methylbenzylamide to (S)-3'-phenylprop-2'-enoyl-4-benzyloxazolidinone, the reactive conformation of the N-acyl oxazolidinone is the anti-s-cis form, facilitating the asymmetric synthesis of a pseudotripeptide.
Davies
Stephen G
SG
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA. steve.davies@chemistry.ox.ac.uk
Hermann
Gesine J
GJ
Sweet
Miles J
MJ
Smith
Andrew D
AD
D000596:Amino Acids / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D018020:Lithium Compounds; D009842:Oligopeptides; D023303:Oxazolidinones