Chlorodicyclohexylborane-mediated aldol additions of alpha,alpha'-dioxygenated ketones.
Boron aldol additions of variously O-protected alpha,alpha'-dioxygenated ketones using dicyclohexylboron chloride and a tertiary amine have been investigated. The stereoselectivity of the process was dependent on the protecting group on the alpha-oxygen atoms. Notably, ketones with bulky silyloxy groups gave syn aldols, most likely via Z enolates. This rules out the participation of chelates during the enolization process, at least in the presence of such sterically crowded protecting groups. An alternative explanation is offered.
Murga
J
J
Departamento de Q. Inorgánica y Orgánica, Universitat Jaume I, Castellón, E-12080 Castellón, Spain.
Falomir
E
E
Carda
M
M
González
F
F
Marco
J A
JA