The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an alpha-amino ester to alpha,beta-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70 degrees C in the presence of catalytic amounts of the nonionic strong bases P(RNCH(2)CH(2))(3)N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.

No abstract

No abstract

No abstract

FETTERLY, B. M.; JANA, N. K.; VERKADE*, J. G.; Tetrahedron 62 (2006) 2-3, p440-p456; Dep. Chem., Iowa State Univ., Ames, IA 50011, USA; Eng.) -Y. Steudel 22-033