126003-97-2

Upstream product

• 7785-26-4 (-)-α-pinene 
• 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 
• 100-46-9 benzylamine 

Downstream Products

• 126004-02-2 (1R,2R,5R)-3-[(E)-(S)-2-(3-Methoxy-phenyl)-1-phenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 126003-98-3 (1R,2R,5R)-3-[(1S)-α-methylbenzylimino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 56613-80-0 D-2-phenylglycinol 
• 109430-87-7 (S)-(+)-2-(3-methoxyphenyl)-1-phenylethylamine 
• 32908-36-4 (S)-cylohexyl(phenyl)methanamine 
• 23459-35-0 R-α-cyclohexylbenzylamine 
• 3082-58-4 (S)-1,2-diphenylethyl amine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 173345-75-0 (S)-N-Boc-1,2-diphenylethylamine 
• 14149-00-9 (S)-1,2-diphenylethylamine hydrochloride 

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.

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 IX: STEREOCONTROLLED SYNTHESIS OF (R)-OR-(S)-2-AMINO-2-PHENYLETHANOL VIA CHIRAL PINANONE KETIMINE TEMPLATE

The asymmetric synthesis of both (R)-and (S)-2-amino-phenylethanols in optical purity >97percent has been achieved by the carbonyl addition of the pinanone ketimine of benzylamine to paraformaldehyde.