NAD(P)+–NAD(P)H models. 84. Stereochemistry controlled by the electronic effect from a sulfinyl group

✍ Scribed by Atsuyoshi Ohno; Norimasa Yamazaki; Akihiro Tsutsumi; Yuji Mikata; Mutsuo Okamura

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 542 KB
• Volume: 6
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520060112

✦ Synopsis

2,3-Dihydro-2,2,4-trimethylthieno[3,2-b]pyridinium

I-oxide iodide (1) has been reacted with various inorganic and organic hydride donors. It has been found that the stereochemistry of reaction is controlled by the orientation of the sulfinyl dipole, and the relative bulkiness of substituents plays no role in determining the reaction face: a reactive hydride donor prefers to attack at the anti-face with respect to the sulfinyl dipole, whereas a less reactive hydride donor prefers to attack at the syn-face.