A stereodivergent approach to amino acids, amino alcohols, or oxazolidinones of high enantiomeric purity.
(-)-Menthone, an inexpensive chiral auxiliary, was used to prepare both enantiomers of alpha-amino acids, amino alcohols, or oxazolidinones. The sequence includes the S(N)2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.
Spino
Claude
C
Département de Chimie, Université de Sherbrooke, 2500 Boulevard Université, Sherbrooke, Quebec, Canada J1K 2R1. claude.spino@usherbrooke.ca
Tremblay
Marie-Claude
MC
Godbout
Cédrickx
C
Gobdout
Cédrickx
C
D000596:Amino Acids / Q000138:chemical synthesis*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D003500:Cyclization; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D000605:Amino Alcohols; D023303:Oxazolidinones