Nickel-Mediated Synthesis of Non-AnomericC-Acyl Glycosidesthrough Electron Donor-Acceptor Complex Photoactivation

被引：16

作者：

Escolano, Marcos ^{[1
]}

Cabrera-Afonso, Maria Jesus ^{[1
]}

Ribagorda, Maria ^{[2
,3
]}

Badir, Shorouk O. ^{[1
]}

Molander, Gary A. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

[2] Univ Autonoma Madrid, Fac Ciencias, Dept Quim, Madrid 28049, Spain

[3] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Madrid 28049, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 07期

关键词：

REDOX-ACTIVE ESTERS; C-GLYCOSIDES; ALKYL; ACIDS;

D O I：

10.1021/acs.joc.1c03041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of nonanomericC-acyl-saccharides has been developed from two different carboxylic acid feedstocks.This transformation is driven by the synergistic interaction of an electron donor-acceptor complex and Ni catalysis. Primary-,secondary-, and tertiary redox-active esters are incorporated as coupling partners onto preactivated pyranosyl- and furanosyl acids,preserving their stereochemical integrity. The reaction occurs under mild conditions, without stoichiometric metal reductants orexogenous catalysts, using commercially available Hantzsch ester as the organic photoreductant.

引用

页码：4981 / 4990

页数：10

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