@Article{IPB-1817,
author = {Rivera, D. G. and Pando, O. and Suardiaz, R. and Coll, F.},
title = {{Studies on the regioselectivity of the Baeyer-Villiger reaction of 3-keto steroids: Conformational effects determine the migration aptitude}},
year = {2007},
pages = {466-473},
journal = {Steroids},
doi = {10.1016/j.steroids.2007.01.002},
volume = {72},
abstract = {A detailed study of the Baeyer-Villiger reaction of 3-ketosteroids has been performed by using m-chloroperoxybenzoic and trifluoroperoxyacetic acids as oxidants. The process was fully regiospecific for 3-keto-5α-steroids with the employ of both peracids, and only partially regioselective for 3-keto-5β-steroids by using trifluoroperoxyacetic acid. Interestingly, the reaction resulted completely unselective for 3-keto-5β-steroids by using m-chloroperoxybenzoic acid. Theoretical studies were performed to explain the regiochemistry of this process, which is suggested to be controlled by conformational effects in the transition state of the Criegee rearrangement.}    
}