Chiral Ferrocenyl P,N-Ligands for Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Esters with β-Ketoesters: Access to Functionalized Chiral 2,3-Dihydrofurans

被引：45
|
作者：
Zhou, Yong [1 ,3 ]
Zhu, Fu-Lin [2 ]
Liu, Zhen-Ting [2 ]
Zhou, Xiao-Mao [1 ,3 ]
Hu, Xiang-Ping [2 ]
机构：
[1] Hunan Acad Agr Sci, Biotechnol Res Ctr, Changsha 410125, Hunan, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[3] Collaborat Innovat Ctr Field Weeds Control, Loudi 417000, Hunan, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 11期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; HIGHLY ENANTIOSELECTIVE SYNTHESIS; FULLY SUBSTITUTED PYRROLES; FEIST-BENARY REACTION; 1,3-DICARBONYL COMPOUNDS; TANDEM REACTION; PRIMARY AMINES; KETO-ESTERS; DIHYDROFURANS; ALCOHOLS;
D O I：
10.1021/acs.orglett.6b01192
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective palladium-catalyzed [3 + 2] cycloaddition of propargylic esters with, beta-ketoesters has been realized by employing a newly developed chiral ferrocene/benzimidazole-based P,N-ligand. This protocol features a good tolerance of functional groups in both propargylic esters and beta-ketoesters, thereby delivering a variety of highly functionalized chiral 2,3-dihydrofurans bearing an exocyclic double bond at the 3-position in good yields and with high enantioselectivities (up to 98% ee).
引用
收藏
页码：2734 / 2737
页数：4
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