Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines

Article abstract of DOI:10.1016/S0040-4020(98)00807-2

Lewis Acid-mediated coupling reactions of (5R, 6S)-2-acetoxy-4- (benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (2a) with allylsilanes (3a-d) proceeded to give the coupling products (4a-b) with moderate to good stereoselectivity. The coupling products (4a-b) were effectively converted into 1-Boc-3- and 4-hydroxypyrrolidines (8a, syn-b, and c).