Protecting-group-free synthesis of 2-deoxy-aza-sugars

Abstract

The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino- L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.