Revision of stereochemical assignments of (2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol

Add time:08/02/2019    Source:sciencedirect.com

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.

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