title: Palladium-catalyzed decarboxylative aza-Michael addition-allylation reactions between allyl carbamates and activated olefins. Generation of quaternary carbon adjacent to secondary amine carbon center.
abstract: The reaction of allyl carbamates with activated olefins in the presence of Pd(PPh3)4 catalyst in THF proceeded smoothly at room temperature to give the corresponding beta,alpha-bisadducts, beta-amino-alpha-allylated products, in high yields. Not only highly activated olefins containing two cyano groups but also 2-cyano enones underwent facile aza-Michael addition--allylation with various allylic carbamates giving the corresponding products in high yields and with high diastereoselectivities. The stereochemistry of the singly formed product was confirmed with the help of X-ray crystallographic technique. It is an excellent method for creating beta-amino alpha-allyl ketones having two contiguous stereocenters: quaternary carbon adjacent to secondary amine carbon center.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
authors.forename: Nitin T
authors.initials: NT
authors.lastname: Patil
authors.forename: Zhibao
authors.initials: Z
authors.lastname: Huo
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Yamamoto