Diastereoselectivity in the alkylations of bicyclic piperidinones

Article abstract of DOI:10.1016/S0040-4039(97)10694-3

The synthesis of substituted [4.3.0] bicyclic lactams derived from 6- oxo-2-hydroxymethylpiperidine is described. The enolate derived flora these systems can be alkylated with a range of reactive electrophiles; the diastereoselectivity which can be achieved depends on the substitution pattern of the oxazolidine ring system and the nature of the alkylating reagent, and can vary from 1:1 to as much as 10:1.