235093-64-8

Upstream product

• 71338-48-2 phenylselanylacetaldehyde 
• 55179-51-6 (-)-aminomenthol 
• 115156-56-4 (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 235094-13-0 1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-propenone 
• 235093-82-0 N-crotyl-2α-(phenylseleno)methyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 235094-17-4 (E)-1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-but-2-en-1-one 
• 235093-81-9 N-allyl-2α-(phenylseleno)methyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 235093-83-1 N-cinnamyl-2α-(phenylseleno)methyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 235093-84-2 N-prenyl-2α-(phenylseleno)methyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 235093-65-9 N-(phenylseleno)ethyl-8-aminomenthol 
• 186597-30-8 (3'R)-8-(3'-methylpyrrolidinyl)menthol 
• 186597-31-9 (3'S)-8-(3'-methylpyrrolidinyl)menthol 
• 235093-93-3 (3'R)-8-(3'-ethylpyrrolidinyl)menthol 
• 235093-96-6 (3'S)-8-(3'-ethylpyrrolidinyl)menthol 
• 235093-95-5 (3'S)-8-(3'-isopropylpyrrolidinyl)menthol 
• 235093-75-1 (3R,3aS,4aR,6R,8aS)-3-Benzyl-6,9,9-trimethyl-decahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazine 
• 235093-72-8 (3S,3aS,4aR,6R,8aS)-3-Benzyl-6,9,9-trimethyl-decahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazine 

Relevant academic research and scientific papers

Regio- and stereoselective 5-exo radical cyclizations on a chiral perhydro-1,3-benzoxazine moiety. An access to enantiopure 3-alkylpyrrolidines

Both enantiomers of chiral, nonracemic 3-alkyl-substituted pyrolidines are prepared by diastereo-selective 5-exo-trig cyclization on (-)-8- aminomenthol-derived perhydro-1,3-benzoxazines used as chiral auxiliaries, followed by elimination of the menthol appendage. The diastereoselective radical cyclization is promoted by tributyltin hydride and occurs on a 3- aza-5-hexenyl-type radical, leading to five-membered rings in high yield. The stereocontrol of the cyclization is strongly influenced by 1,3-allylic strain so that an appropriate substitution pattern on the olefin-acceptor and the presence of a vicinal stereocenter are crucial for achieving good diastereoselectivity. The enantiopure pyrrolidines are obtained in three steps with concomitant recovering of the starting (+)-pulegone auxiliary.

Diastereoselective 5-exo-trig radical cyclisation on N-acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines

N-acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd.