Stereocontrol in the Intramolecular Nitrone Cycloaddition to Vinyl Sulphur Derivatives.

Article abstract of DOI:10.1016/S0957-4166(00)86330-2

The intramolecular cycloaddition to vinyl sulphur derivatives of a series of nitrones featuring an alkyl or alkoxy substituted α-stereocenter on the tether connecting dipol and dipolarophile occurs in a competely stereoselective fashion to give 3',3-anti configurated products.The synthetic potentialities of this reaction is illustrated by the synthesis of a precursor of (d)-biotin.