beta-Hydroxysulfoxides as chiral cyclic ketone equivalents: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones.
The beta-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. carmen.carrenno@uam.es
Pérez-González
Manuel
M
Ribagorda
María
M
Somoza
Alvaro
A
Urbano
Antonio
A