126003-99-4

Upstream product

• 100-46-9 benzylamine 
• 138175-23-2 (1R,2R,5R)-2,6,6-Trimethyl-3-[(E)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 7785-26-4 (-)-α-pinene 
• 126003-96-1 C₁₇H₂₃NO 
• 100-44-7 benzyl chloride 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 
• 126003-96-1 (1S,2S,5S)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 67617-36-1 2α-hydroxy-2,6,6-trimethybicyclo<3.1.1>heptan-3-one oxime 
• 34645-25-5 (R)-(-)-1,2-diphenylethylamine 
• 67553-41-7 pinanone oxime 
• 3082-58-4 (S)-1,2-diphenylethyl amine 
• 173345-75-0 (S)-N-Boc-1,2-diphenylethylamine 
• 14149-00-9 (S)-1,2-diphenylethylamine hydrochloride 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 

Relevant academic research and scientific papers

A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries

(+)-2-hydroxy-3-pinanone ((+)-HyPN,(+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methylamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.

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.