Catalytic Enantioselective N-Nitroso Aldol Reaction of ?,d-Unsaturated d-Lactones.

Organic letters

PubMedID: 22568583

Yanagisawa A, Fujinami T, Oyokawa Y, Sugita T, Yoshida K. Catalytic Enantioselective N-Nitroso Aldol Reaction of ?,d-Unsaturated d-Lactones. Org Lett. 2012;.
A catalytic asymmetric N-nitroso aldol reaction of ?,d-didehydro-d-lactones with nitrosoarenes was achieved using chiral tin dibromide as the chiral precatalyst and sodium ethoxide as the base precatalyst in the presence of ethanol. Optically active a-hydroxyamino ketones with up to 99% ee were regioselectively obtained in moderate to high yields from various d-aryl-substituted ?,d-didehydro-d-valerolactones and o-substituted nitrosoarenes.