32975-62-5

Upstream product

• 50-00-0 formaldehyd 
• 88931-11-7 (S)-(-)-4-phenyl-1,5-diazacyclooctan-2-one 
• 1356849-82-5 methyl (S)-3-[N-(3'-chloropropyl)-N-methylamino]-3-phenylpropanoate 
• 1356849-83-6 methyl (S)-3-[N-(3'-azidopropyl)-N-methylamino]-3-phenylpropanoate 
• 1356849-84-7 C₁₄H₂₂N₂O₂ 
• 1356849-80-3 methyl (3S,αR)-3-[N-( 3'-chloropropyl)-N-(α-methyl-4''-methoxybenzyl)amino]-3-phenylpropanoate 
• 1356849-81-4 methyl (S)-3-(3'-chloropropylamino)-3-phenylpropanoate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1393593-37-7 methyl (3S, αR)-3-[N-( 3'-aminopropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 1393593-36-6 methyl (3S, αR)-3-[N-( 3'-azidopropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 1393593-35-5 methyl (3S, αR)-3-[N-( 3'-chloropropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 1393593-20-8 (R)-N-(3′-chloropropyl)-N-(α-methylbenzyl)amine 
• 1356849-85-8 (R)-N-(3-chloroprop-1-yl)-N-(α-methyl-4'-methoxybenzyl)amine 
• 1393593-52-6 (4S,αR)-4-phenyl-N(5)-(α-methyl-4'-methoxybenzyl)-1,5-diazocan-2-one 

Downstream Products

• 20410-93-9 1,1'-(butane-1,4-diyl)bis[hexahydro-5-methyl-4-phenyl-1,5-diazocin-2(1H)-one] 
• 88931-13-9 (S,S)-1,4-di-[2'-oxo-4'-phenyl-N(5')-methyl-1',5'-diazocan-N(1')-yl]butane 
• 1403934-35-9 (S)-N(1)-(4′-bromobutyl)-4-phenyl-N(5)-methyl-1,5-diazocan-2-one 
• 1393593-69-5 (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one 
• 1393593-66-2 (S,E)-1,4-di[2'-oxo-4'-phenyl-N(5')-methyl-1',5'-diazocan-1'-yl]but-2-ene 
• 1393593-64-0 (S)-N⁽¹⁾-allyl-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one 

Relevant academic research and scientific papers

Asymmetric synthesis of (-)-(S,S)-homaline

The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybe

Asymmetric syntheses of the homalium alkaloids (-)-(S, S)-homaline and (-)-(R, R)-hopromine

The highly diastereoselective conjugate additions of the novel lithium amide reagents lithium (R)-N-(3-chloropropyl)-N-(α-methylbenzyl)amide and lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to α,β-unsaturated esters were used as the key steps in syntheses of the homalium alkaloids (-)-(S,S)-homaline and (-)-(R,R)-hopromine. The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps and 18% overall yield, and the asymmetric synthesis of (-)-(R,R)-hopromine was achieved in 9 steps and 23% overall yield, from commercially available starting materials in each case. These syntheses therefore represent by far the most efficient total asymmetric syntheses of these alkaloids reported to date. A sample of the (4′R,4′′S)-epimer of hopromine was also produced using this approach, which provided the first unambiguous confirmation of its absolute configuration and therefore that of natural (-)-(R,R)-hopromine.

Asymmetric synthesis of 4-phenyl-1,5-diazacyclooctan-2-one using optically active vinyl sulfoxides

Both enantiomers of (S)- and (R)-4-phenyl-1,5-diazacyclooctan-2-ones (7) were synthesized stereoselectively with good optical purity by the asymmetric conjugate addition of pyrazolidine to optically active vinyl sulfoxides, t-butyl (E)-2-[(R)- and (S)-p-tolylsulfinyl]cinnamates, respectively. Starting from 7, a synthesis of optically active homaline was achieved.