Carbohydrate-Derived Chiral Furanosidic α,β-Unsaturated Aldehydes in Conjugate and Diels-Alder Addition Reactions. Steric Hindrance by the Anomeric Substituent

Article abstract of DOI:10.1021/jo00307a018

The title aldehydes (1r, 1s, 2, and 3) underwent virtually diastereospecific conjugate addition by lithium methylcyanocuprate.The bulkiness of the anomeric benzyloxy or methoxy groups direct the attacking nucleophile to the less hindered side of the furan