Asymmetric [3+2] Cycloadditions of Allenoates and Dual Activated Olefins Catalyzed by Simple Bifunctional N-Acyl Aminophosphines

被引:273
作者
Xiao, Hua [1 ]
Chai, Zhuo [2 ]
Zheng, Chang-Wu [2 ]
Yang, Ying-Quan [1 ]
Liu, Wen [1 ]
Zhang, Jun-Kang [2 ]
Zhao, Gang [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; cycloaddition; olefins; organocatalysis; phosphanes; BAYLIS-HILLMAN REACTIONS; ELECTRON-DEFICIENT OLEFINS; MODIFIED ALLYLIC COMPOUNDS; QUATERNARY CARBON CENTERS; METHYL VINYL KETONE; 4+2 ANNULATION; ENANTIOSELECTIVE SYNTHESIS; SULFONATED IMINES; PHOSPHINE; 2,3-BUTADIENOATES;
D O I
10.1002/anie.201000446
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Bifunctional catalyst: Simple bifunctional N-Acyl aminophosphines such as 1 were developed to catalyze the first asymmetric [3+2] cycloaddition between allenoates and dual activated olefins. The cycloaddi- tion reactions afford multifunctional chiral cyclopentenes with exclusive regioselectivity, and good to excellent enantioselectivity and yields. © 2010 Wlley-VCH Verlag GmbH &. Co. KGaA, Weinheim.
引用
收藏
页码:4467 / 4470
页数:4
相关论文
共 85 条
[1]   Synthesis of ruthenium hydride complexes containing beta-aminophosphine ligands derived from amino acids and their use in the H2-hydrogenation of ketones and imines [J].
Abdur-Rashid, K ;
Guo, RW ;
Lough, AJ ;
Morris, RH ;
Song, DT .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :571-579
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]  
[Anonymous], 2003, Angew. Chem
[4]   Design and synthesis of new bidentate phosphoramidite ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc to enones [J].
Boeda, Fabien ;
Rix, Diane ;
Clavier, Herve ;
Crevisy, Christophe ;
Mauduit, Marc .
TETRAHEDRON-ASYMMETRY, 2006, 17 (19) :2726-2729
[5]   Small-molecule inhibitors of protein geranylgeranyltransferase type I [J].
Castellano, Sabrina ;
Fiji, Hannah D. G. ;
Kinderman, Sape S. ;
Watanabe, Masaru ;
de Leon, Pablo ;
Tamanoi, Fuyuhiko ;
Kwon, Ohyun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5843-+
[6]   Asymmetric formation of quaternary carbon centers catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes [J].
Chen, ZG ;
Zhu, GX ;
Jiang, QZ ;
Xiao, DM ;
Cao, P ;
Zhang, X .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5631-5635
[7]   Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles [J].
Chung, Ying Kit ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2225-2227
[8]   Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].
Cowen, Bryan J. ;
Miller, Scott J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+
[9]   Enantioselective catalysis and complexity generation from allenoates [J].
Cowen, Bryan J. ;
Miller, Scott J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116
[10]   Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].
Creech, Gardner S. ;
Kwon, Ohyun .
ORGANIC LETTERS, 2008, 10 (03) :429-432