163460-82-0

Upstream product

• 400782-36-7 t-butyl (+)-3-hydroxy-3-phenyl-2-<(R)-p-tolylsulfinyl>propionate 
• 100-52-7 benzaldehyde 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 400782-30-1 t-butyl (-)-3-hydroxy-3-phenyl-2-<(S)-p-tolylsulfinyl>propionate 

Downstream Products

• 76598-25-9 (S)-(-)-1,5-Diaza-4-phenylbicyclo<4.3.0>nonan-2-one 
• 120686-18-2 (S)-3-amino-3-phenylpropionic acid tert-butyl ester 
• 173398-07-7 (R)-(+)-4-phenyl-1,5-diazacyclooctan-2-one 
• 173398-08-8 (R)-(-)-5-methyl-4-phenyl-1,5-diazacyclooctan-2-one 
• 32975-62-5 (S)-(+)-5-methyl-4-phenyl-1,5-diazacyclooctan-2-one 
• 88931-11-7 (S)-(-)-4-phenyl-1,5-diazacyclooctan-2-one 
• 82359-84-0 1,4-bis<(S)-(-)-2-oxo-4-phenyl-1,5-diazacyclooctanyl>-butane 
• 20410-93-9 1,1'-(butane-1,4-diyl)bis[hexahydro-5-methyl-4-phenyl-1,5-diazocin-2(1H)-one] 
• 180324-14-5 (S)-4-phenyl-1-(2'-cyanoethyl)-1,5-diazacyclononan-2-one 
• 400782-35-6 (S)-(-)-4-phenyl-1-(3'-phthalimidopropyl)-1,5-diazacyclononan-2-one 
• 166373-40-6 (-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one 
• 180324-13-4 (S)-(-)-4-phenyl-1-(3'-aminoethyl)-1,5-diazacyclononan-2-one 
• 53938-05-9 (S)-(-)-celacinnine 
• 112020-25-4 (S)-4-phenyl-1,5-diazacyclononan-2-one 

Relevant academic research and scientific papers

Conjugate addition of 6-membered hydrazine to chiral tert-butyl (E)-2-(p-tolylsulfinyl)cinnamates. Synthesis of (S)-celacinnine

Two enantiomers of the bicyclic lactam, (S)- and (R)-9-phenyl-1,6-diazabicyclo[4.3.0]nonan-7-one (6), were synthesized stereoselectively with high optical purity (95% ee) by the asymmetric conjugate addition-cyclization of piperidazine to chiral vinyl sulfoxides, tert-butyl (E)-2-[(R)- and (S)-p-tolylsulfinyl]cinnamate (4), followed by removal of the p-tolylsulfinyl group with SmI2. The subsequent reductive cleavage of the N-N bond of the bicyclic lactam 6 with sodium in liquid ammonia produced the corresponding 9-membered azalactam, (S)- and (R)-4-phenyl-1,5-diazacyclononan-2-one (7) with 99% and 97% ee, respectively. X-ray crystallography showed that (S)-7 exists exclusively as a trans conformer in the crystal state. Starting from (S)-7, naturally occurring (S)-celacinnine 1 was synthesized with 99% ee employing the ring-expansion reaction via intramolecular transamidation.

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.