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

✍ Scribed by Tsutomu Nonaka; Yoshikazu Kusayanagi

Publisher: Elsevier Science
Year: 1981
Tongue: English
Weight: 567 KB
Volume: 26
Category: Article
ISSN: 0013-4686
DOI: 10.1016/0013-4686(81)85052-9

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✦ Synopsis

Pro&al ketones, which have a chirality center at their /$ositions but are not optically-active, were electrolytically rcdueed at a tncrcuty cathode. It is noticeable that the isomeric ratio of the diastereomeric secondary alcohols formed in the elcctroreduction wss quite different from that in chemical reduction with lithium aluminum hvdride. On the basis of stereoehemieal data obtained, stcreoehemieal course for the reduction were diseu&d.

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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

✍ Tsutomu Nonaka; Yoshikazu Kusayanagi; Toshio Fuchigami 📂 Article 📅 1980 🏛 Elsevier Science 🌐 English ⚖ 510 KB

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