Preparation of optically active amines by a combination of Gabriel synthesis and optical resolution. X-Ray crystal structure of the adduct between (–)-10,10′-dihydroxy-9,9′-biphenanthryl and N-(1-tert-butyl-2-oxoazetidin-3-yl)phthalimide

Abstract

Phthalimides which have a chiral alkyl group on the nitrogen atom, and which can easily be derived from potassium phthalimide and a chiral alkyl halide, were resolved by complexation with an optically active host compound. Decomposition, with hydrazine, of the resolved phthalimides gave optically active amines. Chiral recognition in an inclusion crystal of optically active N-azetidinone-substituted phthalimide and the optically active 10,10′-dihydroxy-9,9′-biphenanthryl host compound was studied by X-ray structure analysis.