334706-50-2

Upstream product

• 55179-51-6 (-)-aminomenthol 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 334706-53-5 N-crotyl-2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-47-3 (2S,7R,9R,10S)-2-(o-bromophenyl)-3-cinnamyl-4,4,7-trimethyl-octahydro-2H-1,3-benzoxazine 
• 334706-52-4 N-cinnamyl-2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-65-5 (1R,2S,5R)-2-[1-((3S,4R)-4-Benzyl-3-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 
• 350508-50-8 N-(o-bromobenzyl)-2α-styryl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-55-3 (3R,4aR,5aS,6R,12aS)-6-Benzyl-3,12,12-trimethyl-2,3,4,4a,6,11,12,12a-octahydro-1H,5aH-5-oxa-11a-aza-naphthacene 
• 350508-42-8 (1R,2S,5R)-2-[1-((3S,4R)-4-Isopropyl-3-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 
• 350508-49-5 N-(o-bromobenzyl)-2α-(2'-methyl-1'-propenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-48-4 N-(o-bromobenzyl)-2α-(1'-propenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-58-6 (1R,2S,5R)-2-[1-((R)-4-Isopropyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 
• 350508-62-2 (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((R)-5-methyl-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-ethyl]-cyclohexanol 
• 203190-44-7 N-(o-bromobenzyl)-2α-vinyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 350508-57-5 (1R,2S,5R)-2-[1-((R)-4-Ethyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 
• 350508-40-6 (1R,2S,5R)-2-[1-((1S,4R)-1,4-Dimethyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 

Relevant academic research and scientific papers

Synthesis of enantiopure mono- and disubstituted tetrahydroisoquinolines by 6-exo radical cyclizations

2-(o-Bromophenyl)-3-allyl- and 2-allyl-3-(o-bromobenzyl)-substituted perhydrobenzoxazines, derived from (-)-8-amino menthol, readily cyclized stereoselectively by reaction with tributyltin hydride in the presence of AIBN. The cyclization compounds were transformed into enantiopure 4-alkyl tetrahydroisoquinolines by reductive ring opening of the N,O-acetal moiety with lithium aluminum hydride. Enantiopure 1,4- and 3,4-dialkyl-substituted tetrahydroisoquinolines were also prepared by reaction of the cyclized compounds with methylmagnesium iodide and subsequent elimination of the menthol appendage.

Diastereoselective tandem 6-exo carbolithiation intramolecular ring opening in (-)-8-aminomenthol-derived perhydrobenzoxazines. A new synthesis of enantiopure 4-substituted tetrahydro isoquinolines and 2-azabenzonorbornanes

Aryllithiums prepared by bromine - lithium interchange in chiral 2-(o-bromophenyl)-substituted perhydro-1.3-benzoxazines participate in the intramolecular 6-exo carbolithiation reaction with unactivated double bonds attached to the nitrogen substituent of