Asymmetric synthesis of functionalized carbocycles and heterocycles.
Anions of 1-halo-4-hexenyl phosphonamides derived from chiral, enantiopure C2 symmetrical 1,2-diamino cyclohexane react at the gamma-position in conjugate addition reactions with alpha, beta-unsaturated carbonyl compounds such as cyclopentenone, 4-(H)-furanone, pyrroline-2-one, and cinnamates to give functionalized adducts. Addition to imines is also possible. The adducts can be transformed into enantiopure or enriched carbocyclic and heterocyclic compounds bearing useable functionality.
Hanessian
S
S
Department of Chemistry, Universite de Montreal, Succursale Centreville, Montreal, Quebec, Canada. hanessia@ere.umontreal.ca
Griffin
A M
AM
Cantin
L D
LD
D002621:Chemistry / Q000379:methods*; D002934:Cinnamates / Q000737:chemistry; D003510:Cyclohexanes / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D006838:Hydrocarbons / Q000138:chemical synthesis*; D008956:Models, Chemical; D008968:Molecular Conformation; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
D002934:Cinnamates; D003510:Cyclohexanes; D003517:Cyclopentanes; D005663:Furans; D006838:Hydrocarbons; D011758:Pyrroles; C013231:pyrroline; C013905:cyclopentenone