Stereochemical studies of the electrolytic reactions of organic compounds—XIII. Electrolytic reduction of ketones having a chirality center at their α-positions to the corresponding diastereomeric alcohols

✍ Scribed by Tsutomu Nonaka; Yoshikazu Kusayanagi; Toshio Fuchigami

• Publisher: Elsevier Science
• Year: 1980
• Tongue: English
• Weight: 510 KB
• Volume: 25
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(80)80022-3

✦ Synopsis

Optically-inactive ketones, which have a chirality center at their a-positions, were electrolytically reduced to the corresponding diastereomeric secondary alcohols. The isomeric ratio of the alcohols depended on the substituent of the ketones and on electrolytic conditions. It is noticeable that a ketone having a cyclohexyl group at the a-position gave the anti-Cram alcohol (the diastereomer expected to form less advantageously from the Cram rule) as a major diastereomer under a variety of electrolytic conditions.

From stereochemical data obtained, stereochemical courses for the reduction were tentatively proposed.