Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of -hydroxyimino cyclic ketones: direct approach to ring-fused hydroxyimino dihydropyransElectronic supplementary information (ESI) available. CCDC 931435. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3ob41001c

• Main Authors: Liu, Luping, Zhang, Dekui, Zhang, Panpan, Jiang, Xianxing, Wang, Rui
• Format: Journal Article
• Language: English
• Published: 24.07.2013
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c3ob41001c

Herein, we have disclosed a catalytic asymmetric 1,5(6)-selective Michael/cyclization reaction of -hydroxyimino cyclic ketones with ,-unsaturated -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. Herein, we have disclosed an catalytic asymmetric 1,5(6)-selective Michael/cyclization reaction of -hydroxyimino cyclic ketones with ,-unsaturated -keto esters to access synthetic useful ring-fused dihydropyrans.