Diastereoselectivity in the addition of organocerium reagents to 4- and 5-oxazolidonecarbaldehydes: Synthesis of syn- and anti-alcohols

Article abstract of DOI:10.1016/S0040-4039(96)01473-6

Chiral non-racemic 4- and 5-oxazolidonecarbaldehydes, typified by 2 and 7, react highly diastereoselectively with organocerium reagents to give moderate to good yields of syn- and anti-alcohols, respectively. Rationalizations for the observed diastereoselectivites are presented. The synthetic potential of this method is exemplified by the synthesis of C-18-D-ribo-phytosphingosine which was obtained as its tetraacetate.