Horner-Wittig reactions of β-aminoalkyl- and β-N-acylaminoalkyldiphenylphosphine oxides: synthesis of N-allyl amines and amides and 5-diphenylphosphinoyl-2-phenyl-5,6-dihydro-4H-1,3-oxazines

Abstract

Lithium derivatives of β-diphenylphosphinoyl-alkyl amines and dilithium derivatives of the corresponding amides combine with aldehydes or ketones in the Horner-Wittig reaction. Separation of the diastereoisomeric intermediates leads to single positional and geometrical isomers of N-allyl amines and amides. Attempted rearrangement of the same intermediates in acid solution gives dihydro-oxazines or, in one case, a γ-N-acylaminoallyl diphenylphosphine oxide.