Asymmetric nitrone-vinyl sulfoxide cycloadditions

Article abstract of DOI:10.1016/S0957-4166(96)00480-6

The cycloaddition of (Z) and (E)-vinyl sulfoxides with cyclic nitrones 1 and 2 is reported. Best diastereoselection is achieved with (Z)-vinyl sulfoxides 7a-d as dipolarophiles. This methodology allows the highly stereoselective synthesis of (+)-sedridine 9a, (-)-hygroline 10 and (-)-(2S)-N-carbomethoxypelletierine 11a.