Asymmetric synthesis of functionalized carbocycles and heterocycles

Anions of 1-halo-4-hexenyl phosphonamides derived from chiral, enantiopure C-2 symmetrical 1,2-amino cyclohexane react at the gamma-position in conjug ate 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 ca n be transformed into enantiopure or enriched carbocyclic and heterocyclic compounds bearing useable functionality. (C) 2000 Wiley-Liss, Inc.