An efficient synthesis of a new series of acyclonucleosides starting from beta-amino alcohols.

A series of new acyclonucleosides analogues 3 has been synthesized very efficiently in three steps starting from beta-amino alcohols 1. The key step of this process is a nucleophilic substitution with various nucleophiles on 2,2'-anhydronucleosides 2. The chemo- and stereoselectivities of this reaction are discussed. AM1 calculations sustained the observed chemoselectivity.

Synthesis of alpha-substituted allylic amines via a modified bruylants reaction

Silver tetrafluoroborate, used as an iminium ion promoter from alpha-amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting alpha-amino nitrile was treated with this silver salt prior to its reaction with the vinylic Grignard. This improvement was not observed in the case of acetylenic Grignards. The reactivity of other vinyl organometallics (M = Zn, Li, Al, Cu, Si) was briefly examined.

An efficient synthesis of pyrimidines from beta-amino alcohols.

[reaction: see text] Pyrimidinones 3 were chemoselectively reduced by using metal-catalyzed hydrogenation and stereoselectively substituted by various nucleophiles. Starting from beta-amino alcohols 1, the overall process allows efficient access to substituted pyrimidines 4 and 6.