Stereoselective aminohomologation of chiral α-alkoxy aldehydes via thiazole addition to nitrones. Application to the synthesis of N-acetyl-D-mannosamine

Article abstract of DOI:10.1016/S0040-4039(00)74694-6

The addition of 2-lithiothiazole to nitrones derived from D-glyceraldehyde and D-arabinose affords anti-adducts from which α-amino aldehydes are revealed by thiazole-to-formyl deblocking. The methodology provides a new synthesis of N-acetyl D-mannosamine