Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3+2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans

doi:10.1039/c7ob02778h

	Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3+2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans
	Li, Kun 1,2; Zhu, Fu-Lin 2; Liu, Zhen-Ting 2; Tong, Jing 1; Hu, Xiang-Ping 2
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2018-02-07
卷号	16 期号:5 页码:742-749
ISSN号	1477-0520
DOI	10.1039/c7ob02778h
文献子类	Article
英文摘要	The enantioselective construction of a quaternary stereocenter in 2,3-dihydrofuran frameworks has been realized via the palladium-catalyzed asymmetric [3 + 2] cycloaddition of tertiary propargylic carbonates with beta-ketoesters enabled by a chiral ferrocene/benzimidazole-based bidentate P, N-ligand. The reaction was significantly promoted by loss of CO2 to irreversibly form p-propargylpalladium or allenylpalladium intermediates. This protocol features a good tolerance of functional groups in both tertiary propargylic carbonates and beta-ketoesters, thereby delivering a variety of highly functionalized chiral 2,3-dihydrofurans bearing a quaternary stereocenter at the 2-position and an exocyclic double bond at the 3-position in good chemical yields and high enantioselectivities (up to 98% ee).
WOS关键词	TRANSITION-METAL-COMPLEXES ; BETA-KETO-ESTERS ; ORGANIC-SYNTHESIS ; ALLYLIC ALKYLATION ; CASCADE REACTIONS ; CARBONATES ; CYCLOADDITION ; CYCLIZATION ; DERIVATIVES ; LIGANDS
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000423787600010
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/168630]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Tong, Jing; Hu, Xiang-Ping
作者单位	1.Liaoning Univ, Coll Chem, Shenyang 110036, Liaoning, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
推荐引用方式 GB/T 7714	Li, Kun,Zhu, Fu-Lin,Liu, Zhen-Ting,et al. Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3+2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2018,16(5):742-749.
APA	Li, Kun,Zhu, Fu-Lin,Liu, Zhen-Ting,Tong, Jing,&Hu, Xiang-Ping.(2018).Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3+2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans.ORGANIC & BIOMOLECULAR CHEMISTRY,16(5),742-749.
MLA	Li, Kun,et al."Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3+2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans".ORGANIC & BIOMOLECULAR CHEMISTRY 16.5(2018):742-749.