Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions

Article abstract of DOI:10.1002/hlca.19960790223

Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%). Catalytic hydrogenolysis