4-acetoxy- and 4-cyano-1,3-dioxanes in synthesis

Alkylations of 4-cyano-1,3-dioxanes (cyanohydrin acetonides) represent a hi ghly practical approach to syn-1,3-diol synthesis. Herein we present a comp rehensive summary of cyanohydrin acetonide chemistry, with particular empha sis on practical aspects of couplings, as well as their utility in natural product synthesis. Both 4-acetoxy-1,3-dioxanes and 4-lithio-1,3-dioxanes ha ve emerged as interesting anti-1,3-diol synthons. The preparation and utili ty of these two synthons are described.