ChemInform Abstract: 1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis. Intramolecular Alkylation Reactions and Stereoselective Synthesis of anti-2,6-Disubstituted Piperidines.

✍ Scribed by D. CRAIG; R. MCCAGUE; G. A. POTTER; M. R. V. WILLIAMS

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199818157

✦ Synopsis

1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis.

Intramolecular Alkylation Reactions and Stereoselective Synthesis of anti-2,6-Disubstituted Piperidines.

-Chiral tetrahydropyridines (I) undergo intramolecular aromatic substitution reactions to give benzofused bicyclic compounds (II) or (VI) depending on the nature of the acidic reagent.

Compound (II) is converted to 2-methyl-6,7-benzomorphan (V) by desulfonylation and reductive methylation.

Similarly the tryptophanderived acyclic precursor undergoes a tandem cyclization on treatment with trimethylsilyl iodide to give the single diastereomeric product (IX), and the anti-2,6-disubstituted piperidine (XII) is achieved by cationic hydrogenation of the tetrahydropyridine (X) and following desulfonylation. -(CRAIG, D.;