Enantioselective reactions of donor/acceptor carbenoids derived from alpha-aryl-alpha-diazoketones.
The reaction of a variety of alpha-aryl-alpha-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh(2)(S-PTAD)(4), generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.
Denton
Justin R
JR
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA.
Davies
Huw M L
HM