Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of α-hydroxyimino cyclic ketones: direct approach to ring-fused hydroxyimino dihydropyrans.

ABSTRACT

Herein, we have disclosed a catalytic asymmetric 1,5(6)-selective Michael/cyclization reaction of α-hydroxyimino cyclic ketones with γ,ß-unsaturated α-keto esters. Unlike the previous catalytic strategies, this reaction provides a convenient 1,5(6)-selective asymmetric pathway to access synthetically useful ring-fused dihydropyrans. In general, high levels of yield, enantio- and diastereoselectivity (up to 99% yield, >99% ee and >20 1 dr) were obtained.