Abstract
The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected α-amino hydroxamic acids have been de- termined in intermolecular hetero Diels-Alder reactions. The cycloaddi- tion reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a vari- ety of compounds of potential biological interest. Molybdenum hexacar- bonyl reduction of the cycloadducts gave optically pure allylic alco- hols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-ally- lically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs
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