STEREOCHEMISTRY OF -SIGMATROPIC REARRANGEMENTS IN THE OXAZOLE SERIES

Article abstract of DOI:10.1016/S0040-4020(01)87623-7

The transfer of chirality from optically active propargyl and cinnamyl N-acyl-C-phenylglycinates to α-branched ketones may be achieved by sigmatropic rearrangements of oxazole intermediates followed by catalytic hydrogenation of the resulting 3-oxazolinones and subsequent reductive ring cleavage.From (R)-4-phenyl-3-buten-1-ol both enantiomers of 1,4-diphenyl-2-methylbutan-1-one (6) could be obtained by sarting either from the (E)- or (Z)-diastereomer of the alcohol.