126003-98-3

Upstream product

• 126003-96-1 (1S,2S,5S)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 126003-96-1 C₁₇H₂₃NO 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 7785-26-4 (-)-α-pinene 
• 100-46-9 benzylamine 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 

Downstream Products

• 67617-36-1 2α-hydroxy-2,6,6-trimethybicyclo<3.1.1>heptan-3-one oxime 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 67553-41-7 pinanone oxime 
• 1289376-23-3 (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Relevant academic research and scientific papers

Chiral imines and amines based on 2-hydroxypinan-3-one

The new chiral derivatives of benzylamine and 2α-hydroxypinan-3-one (1R,2R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1] heptan-2-ol (2), (1S,2S,3S,5S)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1] heptan-2-ol (3), and (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6- trimethylbicyclo[3.1.1]heptan-2-ol (4) were synthesized and characterized. It was shown that reduction of the benzylimines by sodium triacetoxyborohydride formed stereoselectively 3β-substituted pinanamines.

ASYMMETRIC SYNTHESIS VIII: ENANTIONSELECTIVE SYNTHESIS OF (R) OR (S)-α-SUBSTITUTED BENZYLAMINES VIA CHIRAL PINANONE KETIMINE TEMPLATE

An excellent asymmetric synthesis of both (R) and (S)-α-substituted benzylamines in optical purity 90.4 - 99.9percent has been achieved by alkylation of a chiral ketimine, prepared from pinanone and benzylamine.Diastereoselectivity in the alkylation is not dependent on the alkyl halides.