Catalyst-Directed Diastereoselectivity in Hydrogenative Couplings of Acetylene to a-Chiral Aldehydes: Formal Synthesis of All Eight L-Hexoses.

[摘要]：Hydrogenative coupling of acetylene to a-chiral aldehydes using enantiomeric rhodium catalysts ligated by (S)-MeO-BIPHEP and (R)-MeO-BIPHEP delivers the diastereomeric products of carbonyl-(Z)-butadienylation with good to excellent levels of catalyst directed diastereofacial selectivity. Diastereomeric L-glyceraldehyde acetonide adducts were converted to the four isomeric enoates, e.g. I, representing a formal synthesis of all eight L-hexoses.

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