Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone

Regioselective Michael addition of nitro and heterocyclic compounds to levoglucosenone, 1, is effectively catalyzed by amines and also by cathodic electrolysis. In comparison to the base-catalyzed reaction, it was found that under electrochemical conditions the reaction proceeds under milder conditi...

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Veröffentlicht in:Journal of organic chemistry 1996-12, Vol.61 (25), p.8786-8791
Hauptverfasser: Samet, Alexander V, Niyazymbetov, Murat E, Semenov, Victor V, Laikhter, Andrei L, Evans, Dennis H
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container_end_page 8791
container_issue 25
container_start_page 8786
container_title Journal of organic chemistry
container_volume 61
creator Samet, Alexander V
Niyazymbetov, Murat E
Semenov, Victor V
Laikhter, Andrei L
Evans, Dennis H
description Regioselective Michael addition of nitro and heterocyclic compounds to levoglucosenone, 1, is effectively catalyzed by amines and also by cathodic electrolysis. In comparison to the base-catalyzed reaction, it was found that under electrochemical conditions the reaction proceeds under milder conditions and with higher yields. Cathodically-initiated Michael addition of thiols to levoglucosenone using small currents produces the previously unknown threo addition product in several instances. The normal erythro isomer, identified as the kinetic product, tends to be formed when large currents are used. In contrast, slow, low current electrolyses promote equilibration of the two forms so that erythro can be converted to threo by the retro reaction and readdition. Addition of 2-naphthalenethiol to (R)-(+)-apoverbenone is also reported.
doi_str_mv 10.1021/jo961019g
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title Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone
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