Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

被引:118
作者
Chen, Jianhui [1 ]
Chen, Chenhui [1 ]
Ji, Chonglei [1 ]
Lu, Zhan [1 ]
机构
[1] Zhejiang Univ, Dept Chem, 866 Yuhangtang Rd, Hangzhou 310058, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE HYDROGENATION; ALKENE HYDROGENATION; 1,1-DISUBSTITUTED ALKENES; ARYL CHLORIDES; COMPLEXES; IRON; HYDROBORATION; LIGANDS; OLEFINS;
D O I
10.1021/acs.orglett.6b00453
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.
引用
收藏
页码:1594 / 1597
页数:4
相关论文
共 65 条
[1]   Synthesis and Antimitotic and Tubulin Interaction Profiles of Novel Pinacol Derivatives of Podophyllotoxins [J].
Abad, Andres ;
Lopez-Perez, Jose L. ;
del Olmo, Esther ;
Garcia-Fernandez, Luis F. ;
Francesch, Andres ;
Trigili, Chiara ;
Barasoain, Isabel ;
Andreu, Jose M. ;
Fernando Diaz, J. ;
San Feliciano, Arturo .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (15) :6724-6737
[2]   APPLICATIONS OF AMMONIUM FORMATE CATALYTIC TRANSFER HYDROGENATION .6. ANALYSIS OF CATALYST, DONOR QUANTITY, AND SOLVENT EFFECTS UPON THE EFFICACY OF DECHLORINATION [J].
ANWER, MK ;
SHERMAN, DB ;
RONEY, JG ;
SPATOLA, AF .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1284-1289
[3]   Distinctive Meta-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation [J].
Bess, Elizabeth N. ;
Sigman, Matthew S. .
ORGANIC LETTERS, 2013, 15 (03) :646-649
[4]   Remotely Controlled Iridium-Catalyzed Asymmetric Hydrogenation of Terminal 1,1-Diaryl Alkenes [J].
Besset, Tatiana ;
Gramage-Doria, Rafael ;
Reek, Joost N. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (34) :8795-8797
[5]  
Bianchini C, 2003, EUR J INORG CHEM, P1620
[6]   Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].
Billingsley, Kelvin L. ;
Barder, Timothy E. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363
[7]   Iron-Catalyzed Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes [J].
Chen, Jianhui ;
Cheng, Biao ;
Cao, Minyi ;
Lu, Zhan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (15) :4661-4664
[8]   Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes [J].
Chen, Jianhui ;
Xi, Tuo ;
Ren, Xiang ;
Cheng, Biao ;
Guo, Jun ;
Lu, Zhan .
ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (11) :1306-1309
[9]   Iminopyridine Oxazoline Iron Catalyst for Asymmetric Hydroboration of 1,1-Disubtituted Aryl Alkenes [J].
Chen, Jianhui ;
Xi, Tuo ;
Lu, Zhan .
ORGANIC LETTERS, 2014, 16 (24) :6452-6455
[10]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652