Insights into the Electrochemical Reductive Cyclization of α,β-Unsaturated Carbonyl Derivatives
✍ Scribed by Paul G. Gassman; Changjin Lee
- Book ID
- 104229793
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 272 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A series of acyclic and cyclic Q-unsaturated esters bearing tethered mesylate leaving groups have been electrochemically reduced to give synthetically useful yields of monocyclic and bicyclic esters via attack of the p-carbon of the a&unsaturated ester on the carbon bearing the mesylated moiety.
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Li(sec-Bu)JIH-mediatedreductive cyclization of opticatly pure 8-((S)-p-tolylsultinyI)-(2E,7Z@ctadienoate 9 and 7-(p-tolylsulfinyl)-2,6-heptadienoate 16 affordedtr-ans-2-((mtolylsulfmyl)methyl)cyclohexane-1-carboxylate and tmns-2-(@tolylsulfinyl)merhyl)cyclopentane-I-carboxyhte, w spectively, as a si