Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Article abstract of DOI:10.1016/0040-4039(96)00205-5

The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.