Cross-aldol reactions of levoglucosenone and its derivatives with cyclohex-1-en-1-ol ethers

Autor:	A. R. Tagirov, L. Kh. Faizullina, Yu. S. Galimova, Sh. M. Salikhov, Farid A. Valeev, Leonid V. Spirikhin
Rok vydání:	2017
Předmět:	Trimethylsilyl 010405 organic chemistry Organic Chemistry Acetal Cyclohexanone Ether 010402 general chemistry 01 natural sciences 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Aldol reaction Intramolecular force Moiety Organic chemistry
Zdroj:	Russian Journal of Organic Chemistry. 53:1053-1059
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428017070156
Popis:	The reaction of levoglucosenone with cyclohex-1-en-1-yl trimethylsilyl ether under Mukaiyama reaction conditions gave [1 + 2]-Michael–aldol condensation product with participation of the acetal center. The reaction was accompanied by opening of the 1,6-anhydro bridge and intramolecular hemiketalization by the hydroxy group of the 2-oxocyclohex-1-enyl fragment. Under analogous conditions, dihydrolevoglucosenone gave rise to four diastereoisomeric 1,2-addition products. Internal cyclohex-1-en-1-ol ether obtained by treatment of the Michael adduct of levoglucosenone and cyclohexanone with Ac2O–ZnCl2 underwent intramolecular Mukaiyama reaction involving substituted α-carbon atom of the cyclohexanone fragment and acetal moiety to afford spiro derivative and product of subsequent AdE1 acetylation of intermediate α′-cyclohexenyl ether fragment.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6d5fdedfba3a2b873873f7d9e3f58545 https://doi.org/10.1134/s1070428017070156 Zobrazit plný text záznamu Plný text ve formátu PDF