A practical method for preparation of optically pure oxazaborolidines from α-Pinene

Synthesis of Optically Active, Cyclic α‐Hydroxy Ketones and 1,2‐Diketones from Verbenone Epoxide

“…-Oxygen-containing monoterpenes from the pinane series are commercially available compounds of high optical purity, and may serve as precursors of biologically active compounds [1] and intermediates in asymmetric synthesis [2]. In acidic media, they generally easily undergo numerous transformations, affording complex mixtures of products [3].…”

New PHOX ligands monoterpene derivatives and their application in catalytic transfer hydrogenation of ketones

“…In extension to our studies we decided to examine the influence of monoterpene structure on enantioselectivity of the reduction. We commenced our new PHOX ligand synthesis from (-)-α-pinene which was transformed to the appropriate amino alcohol 10 [24] in few steps. Then 10 was converted to amide 11 in reaction with 2-bromobenzoyl chloride in 64% yield.…”

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

“…The preparation and some synthetic applications of optically pure 3-amino-2-hydroxypinane have been reported by different authors. 11,12 Monoterpene-fused 1,3-oxazines have also been used as catalysts for enantioselective allylic substitution. 13 In an earlier work, we reported the transformations of enantiomerically pure α-pinene to monoterpene-fused saturated 1,3-heterocycles.…”