Michael Adduct of Levoglucosenone and Cyclohexanone. Chiral Protection of Hydroxy Group in Stereoselective Transformations of Glycol Aldehyde

A. R. Tagirov; L. Kh. Fayzullina; D. R. Enikeeva; Yu. S. Galimova; Sh. M. Salikhov; F. A. Valeev

doi:10.1134/S1070428018050093

Michael Adduct of Levoglucosenone and Cyclohexanone. Chiral Protection of Hydroxy Group in Stereoselective Transformations of Glycol Aldehyde

Authors: Tagirov A.R.¹, Fayzullina L.K.¹, Enikeeva D.R.², Galimova Y.S.¹, Salikhov S.M.¹, Valeev F.A.¹
Affiliations:
1. Ufa Institute of Chemistry
2. Ufa State Petroleum Technical University
Issue: Vol 54, No 5 (2018)
Pages: 726-733
Section: Article
URL: https://bakhtiniada.ru/1070-4280/article/view/217787
DOI: https://doi.org/10.1134/S1070428018050093
ID: 217787

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Abstract

One of hydroxy groups of ethylene glycol was protected by hemiketal, obtained by treating Michael adduct of levoglucosenone and cyclohexanone with reagents system Me₃SiCl‒NaI, while the other one was oxidized by Collins method. Stereocontrol in reactions of 1,2-addition to the obtained aldehyde was investigated (in reactions of Grignard, Henry, and Reformatsky).