Synthesis of Chiral C₂-Symmetric 1,10-Phenanthrolines from Naturally Occurring Monoterpenes

Abstract

A convenient procedure for the preparation of chiral C₂-symmetric 1,10-phenanthrolines bearing a chiral framework in the form of a cycloalkeno-condensed substituent in the 2,3- and 8,9-positions of the heterocycle is reported. Starting from the 2-benzyloxycyclohexanone, four 1,10-phenanthrolines derived from (-)-β-pinene, (+)-α-pinene, (-)-isopinocampheol, and (+)-camphor were prepared according to a method based on a double Michael-aza­annulation-aromatization sequence.

Key words

nitrogen heterocycles - 1,10-phenanthrolines - nitrogen ligands - bidentate ligands - Michael additions

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