Palladium/L-Proline-Catalyzed Enantioselective α-Arylative Desymmetrization of Cyclohexanones

被引:101
作者
Liu, Ren-Rong [1 ]
Li, Bao-Le [1 ]
Lu, Jun [1 ]
Shen, Chong [1 ]
Gao, Jian-Rong [1 ]
Jia, Yi-Xia [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
HETEROCYCLIC CARBENE LIGANDS; TRANSITION-METAL; CROSS-COUPLINGS; ALLYLIC ALKYLATION; DUAL CATALYSIS; ARYL HALIDES; ALDEHYDES; ALLYLATION; KETONES; AMINE;
D O I
10.1021/jacs.6b01214
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly enantioselective palladium/L-proline-catalyzed alpha-arylative desymmetrization of cyclohexanones was developed. The new strategy for alpha-arylation reaction led to a series of optically active morphan derivatives bearing a-carbonyl tertiary stereo centers in good yields with excellent enantioselectivities (up to 99% ee).
引用
收藏
页码:5198 / 5201
页数:4
相关论文
共 61 条
[1]   Direct Regiospecific and Highly Enantioselective Intermolecular a-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts [J].
Afewerki, Samson ;
Ibrahem, Ismail ;
Rydfjord, Jonas ;
Breistein, Palle ;
Cordova, Armando .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) :2972-2977
[2]   Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].
Allen, Anna E. ;
MacMillan, David W. C. .
CHEMICAL SCIENCE, 2012, 3 (03) :633-658
[3]   Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4260-4263
[4]   Total Synthesis of (+)- Madangamine D [J].
Ballette, Roberto ;
Perez, Maria ;
Proto, Stefano ;
Amat, Mercedes ;
Bosch, Joan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (24) :6202-6205
[5]   Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].
Bellina, Fabio ;
Rossi, Renzo .
CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146
[6]   Enantioselective α-Arylation of N-Acyloxazolidinones with Copper(II)-bisoxazoline Catalysts and Diaryliodonium Salts [J].
Bigot, Aurelien ;
Williamson, Alice E. ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) :13778-13781
[7]   Synthesis of 2-Azabicyclo[3.3.1]nonanes [J].
Bonjoch, Josep ;
Diaba, Faiza ;
Bradshaw, Ben .
SYNTHESIS-STUTTGART, 2011, (07) :993-1018
[8]   Catalytic Enantioselective α-Arylation of Carbonyl Compounds [J].
Burtoloso, Antonio C. B. .
SYNLETT, 2009, (02) :320-327
[9]   Nickel-catalyzed asymmetric α-arylation of ketone enolates [J].
Chen, GS ;
Kwong, FY ;
Chan, HO ;
Yu, WY ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2006, (13) :1413-1415
[10]   Gold meets enamine catalysis in the enantioselective α-allylic alkylation of aldehydes with alcohols [J].
Chiarucci, Michel ;
di Lillo, Marzia ;
Romaniello, Alessandro ;
Cozzi, Pier Giorgio ;
Cera, Gianpiero ;
Bandini, Marco .
CHEMICAL SCIENCE, 2012, 3 (09) :2859-2863