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Asymmetric synthesis of functionalized carbocycles and heterocycles
S Hanessian1, A M Griffin, L D Cantin
1Department of Chemistry, Universite de Montreal, Succursale Centreville, Montreal, Quebec, Canada. hanessia@ere.umontreal.ca
Chirality
|May 29, 2000
Abstract:
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.