Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides

Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides Full article

Journal

Organic chemistry frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2021, Volume: 8, Number: 12, Pages: 3091-3101 Pages count : 11 DOI: 10.1039/d1qo00494h

Authors

Vera A. Vil ^1,2 , Gorlov Evgenii S. ¹ , Yu Bing ³ , Terent'ev Alexander O. ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russian Federation
2	All-Russian Research Institute for Phytopathology B. Vyazyomy, Moscow Region, Russian Federation
3	Green Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. China

An acetal fragment is a well-known protective group which does not activate the neighboring α-position. Selective functionalization of the non-activated acetal α-position with formal retaining of the acetal fragment was realized using cyclic diacyl peroxides. The discovered oxidative C–O coupling of cyclic diacyl peroxides with acetals leads to α-acyloxy acetals with a free carboxylic acid group in 42–85% yields. The reaction probably proceeds via in situ enol ether formation, oxidative [5 + 2] cycloaddition, and the recovery of the acetal fragment.

Vera A. Vil , Gorlov E.S. , Yu B. , Terent'ev A.O.
Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides
Organic chemistry frontiers. 2021. V.8. N12. P.3091-3101. DOI: 10.1039/d1qo00494h WOS Scopus OpenAlex

Web of science:	WOS:000641276400001
Scopus:	2-s2.0-85108027686
OpenAlex:	W3152799891

DB	Citing
OpenAlex	8
Web of science	8
Scopus	9