Addition of Enolates and Silyl Enol Ethers of Cycloalkanones to Levoglucosenone in the Presence of Lewis Acids


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The addition of lithium enolates and TMS ethers of cyclohexanone and cyclododecanone to levoglucosenone in the presence of Lewis acids was studied. It was established that the optimal way to obtain of Michael adducts involves the reaction levoglucosenone at −78°C with lithium enolates of cyclohexanone and cyclododecanone in the presence of ZnCl2. Additional amounts of Michael adducts can be obtained by treatment of 1,2-adducts with lithium diisopropylamine. 1,2-Adducts are best prepared by the reaction of the corresponding lithium enolates with levoglucosenone in the presence of Ti(Oi-Pr)4.

作者简介

Y. Khalilova

Ufa Institute of Chemistry, Ufa Research Center

Email: sinvmet@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Republic of Bashkortostan, 450054

L. Faizullina

Ufa Institute of Chemistry, Ufa Research Center

编辑信件的主要联系方式.
Email: sinvmet@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Republic of Bashkortostan, 450054

F. Valeev

Ufa Institute of Chemistry, Ufa Research Center

Email: sinvmet@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Republic of Bashkortostan, 450054

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