Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol   Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones

doi:10.1021/jacs.5b04049

CORC > 北京大学 > 化学与分子工程学院

	Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones
	Yang, Bin-Miao ; Cai, Pei-Jun ; Tu, Yong-Qiang ; Yu, Zhi-Xiang ; Chen, Zhi-Min ; Wang, Shuang-Hu ; Wang, Shao-Hua ; Zhang, Fu-Min
刊名	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
	2015
关键词	BRONSTED ACID STEREOSELECTIVE-SYNTHESIS SEMIPINACOL REARRANGEMENT (-)-CALYCIPHYLLINE N CYCLIZATION CATALYSIS ELECTROCYCLIZATION ACTIVATION RESOLUTION DIENONES
DOI	10.1021/jacs.5b04049
英文摘要	A novel organocatalytic asymmetric tandem Nazarov cyclization/semipinacol rearrangement reaction using "unactivated" substrates has been developed, generating a series of chiral spiro[4.4]nonane-1,6-diones in up to 96% yield and 97% enantiomeric excess. Significantly, it is the first direct example for asymmetric synthesis of cydopentanones with four stereocenters using Nazarov cyclization. DFT calculations have been applied to understand the reaction mechanism, stereochemistry, and substituent effects.; Natural Science Foundation of China [21202073, 21290180, 21272097, 21372104, 21472077, 21232001]; "111" Program of MOE; MOST [2012ZX 09201101-003]; SCI(E); EI; PubMed; ARTICLE; tuyq@lzu.edu.cn; 26; 8344-8347; 137
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/418545]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Yang, Bin-Miao,Cai, Pei-Jun,Tu, Yong-Qiang,et al. Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2015.
APA	Yang, Bin-Miao.,Cai, Pei-Jun.,Tu, Yong-Qiang.,Yu, Zhi-Xiang.,Chen, Zhi-Min.,...&Zhang, Fu-Min.(2015).Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY.
MLA	Yang, Bin-Miao,et al."Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015).