Enantioselective deprotonation of 8-oxabicyclo[3.2.1]octan-3-one systems using homochiral lithium amide bases

Abstract

The asymmetric transformation of oxabicyclic ketones 6 and 7 into non-racemic enol silanes 12 (88% ee) and 10 (85% ee), respectively, was achieved using the homochiral lithium amide base 4. Conversion of 10 into a known key intermediate 15 for C-nucleoside synthesis was possible in a highly efficient two step sequence. © 1993.