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Opposite signs of specific rotation are reported in the literature for (4S,5S)-(2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol. The correct assignment was made by unambiguous synthesis of the title compound via the reaction of (S)-O-TBS-mandelic aldehyde with vinyl magnesium chloride, separation of diastereomeric (1S,2S)- and (1S,2R)-1-phenyl-but-3-ene-1,2-diols, and transformation of (1S,2S)-diol into authentic (4S,5S)-(2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol. [Copyright &y& Elsevier]

The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti–anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. [Copyright &y& Elsevier]

Abstract: The reaction of 3-bromo-propenyl acetate with the Garner aldehyde promoted by zinc or indium metal is studied in different solvents; besides the stereoselectivity, attention is focused on a comparative environmental assessment of different experiments carried out in NH4Cl, THF or DMF, using green chemistry metrics and a qualitative analysis of environmental risks. [Copyright &y& Elsevier]