Studies on novel and chiral 1,4-dihydropyridines. IV. Mechanistic aspects of the asymmetric reduction with chiral NADH model compounds, (SS)-3-(p-tolylsulfinyl)-1,4-dihydropyridines

✍ Scribed by Satoshi Obika; Toshihiko Nishiyama; Satoshi Tatematsu; Kazuyuki Miyashita; Takeshi Imanishi

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 537 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00072-0

✦ Synopsis

In the reduction of ketones with NADH mimics, (Ss)-l-substituled 3-(p-tolylsulfinyl)-1,4-dihydropyridines 1, the stereospecific transfer of one of the C-4 hydrogens, which is syn to the S-O bond, was experimentally revealed to be involved by employing the 2-methyl derivative 2 and the 4-deuterated derivatives 3a and 3b. The transition state model of this reaction was also proposed by consideration of the results obtained.