Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)-H Arylation of Glycosides

被引：44
|
作者：
Probst, Nicolas [1 ]
Grelier, Gwendal [2 ]
Dahaoui, Slimane [3 ]
Alami, Monad [1 ]
Gandon, Vincent [4 ,5 ]
Messaoudi, Samir [1 ]
机构：
[1] Univ Paris Saclay, CNRS, Univ Paris Sud, BioCIS, F-92290 Chatenay Malabry, France
[2] Univ Paris Saclay, CNRS, Univ Paris Sud, Inst Chim Subst Nat,UPR 2301, 1 Av Terrasse, F-91198 Gif Sur Yvette, France
[3] Univ Lorraine, Fac Sci & Technol, CNRS,UMR UL 7036, Cristallog Resonance Magnet & Modelisat CRM2, BP 70239,Blvd Aiguillettes, F-54506 Vandoeuvre Les Nancy, France
[4] Univ Paris Saclay, Ecole Polytech, CNRS,UMR 9168, LCM, Route Saclay, F-91128 Palaiseau, France
[5] Univ Paris Saclay, Univ Paris Sud, CNRS,UMR 8182, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France
来源：
ACS CATALYSIS | 2018年 / 8卷 / 09期
关键词：
C(sp(3))-H activation; carbohydrate; palladium catalysis; C-glycosides; DFT calculations; PALLADIUM-CATALYZED ARYLATION; C-H FUNCTIONALIZATION; STEREOSELECTIVE-SYNTHESIS; PERACETYLATED GLYCALS; COUPLING REACTIONS; ARYLBORONIC ACIDS; ARYL GLYCOSIDES; BOND ACTIVATION; DIRECTING GROUP; DERIVATIVES;
D O I：
10.1021/acscatal.8b01617
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
We report herein the diastereoselective C(sp(3))-H arylation of glycosides. A wide range of beta- and alpha-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.
引用
收藏
页码：7781 / 7786
页数：11
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