Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir

An
efficient method to construct chiral acyclic nucleosides via
Sharpless asymmetric dihydroxylation of N-allylpyrimidines
or N-alkenylpurines is reported. A range of chiral
acyclic nucleosides with two adjacent hydroxyl groups present on the
side chains could be produced in good yields (up to 97% yield) and
excellent enantioselectivities (90–99% ee). The synthetic utility
of the reaction was demonstrated by the catalytic asymmetric synthesis
of (S)-Cidofovir and (R)-Buciclovir.

一种构建手性非环状核苷的效率方法被报道，该方法通过Sharpless不对称二羟基化N-烯丙基嘧啶或N-烯丙基嘌呤实现。能够以良好的产率（高达97%）和优异的立体选择性（90%-99%ee）合成一系列具有相邻羟基基团的手性非环状核苷。该反应的合成应用通过(S)-Cidofovir和(R)-Buciclovir的催化不对称合成得到验证。