Abstract

The outcome and stereochemical aspects of 1,4-conjugate addition of thiophenols, α-aminoacid derivatives and hydrazoic acid to chiral (2 S)-hydroxymethyl-dihydropyridone 3 is presented. Subsequent reduction with NaBH 4 provided predominantly the kinetically favored axial 3-piperidinol adducts. The stereochemistry of the products, which depends on electrostatic interaction and steric hindrance, was revealed by 1H NMR and 2D NOESY spectroscopic analysis.

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