The Stereochemistry of the Hydroboration of 2- and 3-Methylene-5α-androstanes
Abstract
The exo facial selectivity in the hydroboration of 2-, 3- and 4-methylene-5α-androstanes is rationalized in terms of the easier steric access and a hyperconjugative interaction of the alkene with the adjacent axial C–H bonds enhancing the electron density on one face of the alkene.