From 1-(Silyloxy)butadiene to 4-Amino-4-deoxy-DL-erythrose and to 1-Amino-1-deoxy-DL-erythriol Derivatives via hetero-Diels-Alder Reactions with Acylnitroso Dienophiles

Article abstract of DOI:10.1002/hlca.19910740806

Acylnitroso dienophiles 4 reacted instantly with 1-(silyloxy)butadiene 5α and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table 1). cis-Hydroxylation of these primary cycloadducts with OsO4 (catalyst) occurred stereospecifically and in high yield (-> 8 and 9, resp.: Scheme 2).It was followed by reductive ring cleavage to give either 1-amino-1-deoxy-DL-erythriol or 4-amino-4-deoxy-DL-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4).