ChemInform Abstract: Enantiospecific Formation of trans-1,3-Disubstituted Tetrahydro-β- carbolines by the Pictet-Spengler Reaction and Conversion of cis Diastereomers into Their trans Counterparts by Scission of the C-1/N-2 Bond.

✍ Scribed by E. D. COX; L. K. HAMAKER; J. LI; P. YU; K. M. CZERWINSKI; L. DENG; D. W. BENNETT; J. M. COOK; W. H. WATSON; M. KRAWIEC

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199718151

✦ Synopsis

Enantiospecific Formation of trans-1,3-Disubstituted Tetrahydro-βcarbolines by the Pictet-Spengler Reaction and Conversion of cis Diastereomers into Their trans Counterparts by Scission of the C-1/N-2 Bond.

-The factors which effect the stereoselective formation of trans-products in the Pictet-Spengler condensation of aldehydes with tryptophan derivatives is examined. The presence of a benzyl group at the Nb-nitrogen atom alters the diastereochemical outcome to provide 100% trans stereoselectivity when the cyclization is carried out with cyclohexanecarboxaldehyde. Upon exposure to acid the diastereomeric ratio shifts to provide the more stable trans diastereomers. -(COX, E.