370102-66-2

Upstream product

• 125330-79-2 1-[2-hydroxy-2-(4-methylthiophenyl)]ethanoyl-2-phenylpyrrolidine 
• 700-91-4 2-phenyl-1-pyrroline 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 93-89-0 benzoic acid ethyl ester 
• 109086-16-0 2-hydroxy-2-(4-methylthiophenyl)ethanoic acid 
• 3446-89-7 4-(Methylthio)benzaldehyde 

Downstream Products

• 120809-07-6 (6S,10bR)-6-(4-Methylsulfanyl-phenyl)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinolin-6-ol 
• 120809-07-6 (6S,10bS)-6-(4-Methylsulfanyl-phenyl)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinolin-6-ol 
• 103729-16-4 (+)-McN-5652 
• 90390-64-0 trans-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline 
• 90390-64-0 cis-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline 
• 1035802-97-1 6-Hydroxy-6-(4-methylsulfanyl-phenyl)-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one 

Relevant academic research and scientific papers

The structure of McN-5652

The configuration of the diastereoisomers of 6-(4-methylthiophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline 1 (McN-5652) is determined and unequivocally assigned by NMR spectroscopy (NOE measurements) and an X-ray structural analysis of the trans diastereoisomer. The enantiomers of cis-1 are separated by preparative HPLC on a chiral phase. One of the enantiomers of cis-1 represents the precursor for imaging the serotonin 5-HT transporter with positron emission tomography (PET).

Metal-Free Formal Oxidative C?C Coupling by In Situ Generation of an Enolonium Species

Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C?C coupling.