Stereoselective synthesis of amino ketones of the pinane series

Abstract

At present, enantiomerically pure α-pinene and camphor derivatives are widely used in asymmetric syntheses as chiral auxiliaries [1], building blocks [2, 3], and chiral ligands [4]. For example, terpene amino alcohols derived from 2α-hydroxypinan-3-one, were studied as enantioselective ligands in the ruthenium-catalyzed reduction of acetophenone [5], while palladium chelates with bornane diimines and diamines efficiently catalyzed asymmetric allylic substitution reactions [6]. According to published data, search for new enantiomerically pure ligands on the basis of commercially available initial compounds is a topical problem. We previously reported the synthesis of chiral imines and amines from 2α-hydroxypinan-3-one [7]. The resulting nitrogen-containing derivatives were successfully used as ligands to obtain various palladium complexes [8, 9].