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Diastereoselective aza-Wacker cyclization of O-allyl hemiaminals under aerobic conditions enables efficient access to 1,2-aminoalcohol derivatives from allylic alcohols. The scope of this method is presented and its utility is highlighted in a streamlined synthesis of the biologically important aminosugar (−)-acosamine. Cbz=benzyloxycarbonyl, TBDPS=tert-butyldiphenylsilyl, TBS=tert-butyldimethylsilyl.
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Weinstein et al. (2013) studied this question.
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