N-trimethylsilyloxyenamines as new aldehyde enolate synthons: general, efficient and diastereoselective aldol reaction with ketals and acetals.
(E)-N-trimethylsilyloxyenamines, easily accessible from aldonitrones, proved to be excellent nucleophiles in TMSOTf-induced diastereoselective aldol reaction, both with ketals and acetals, proceeding via an extended transition state and leading to a new aldol C-C-bond in the aldonitrone products, that can be readily hydrolysed to the corresponding aldehydes.
Sonawane
Manoj R
MR
Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, v. v. i., Flemingovo nam. 2, 16610 Prague 6, Czech Republic.
Císarová
Ivana
I
Lyapkalo
Ilya M
IM