Diasteroselective and Enantioselective Ir-Catalyzed Allylic Substitutions of 1-Substituted 1-Fluoro-1-(arenesulfonyl)methylene Derivatives

被引:15
作者
Chen, Jiteng [1 ,2 ]
Zhao, Xiaoming [1 ,2 ]
Dan, Wenyan [1 ,2 ]
机构
[1] Tongji Univ, Shanghai Key Lab Chem Assessment & Sustainabil, Sch Chem Technol & Engn, 1239 Siping Rd, Shanghai 200092, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
ALLYLATION REACTION; ALKYLATION; ENANTIO; FLUORINATION; DIASTEREO;
D O I
10.1021/acs.joc.7b01782
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
diasteroselective and enantioselective Ir-catalyzed allylic substitutions of 1-substituted 1-fluoro-1-(arenesulfonyl)methylene derivatives are presented, which afford the fluorinated allyl products with two chirality centers. The steric demand of 1-substituted 1-fluoro-1-(arenesulfonyl)methylene derivatives and allylic substrates has a great influence on the dr values of these reactions. The transformation of the branched allyl product into the fluorinated 3,4-dihydro-2H-pyrrole 1-oxide was discussed, as well.
引用
收藏
页码:10693 / 10698
页数:6
相关论文
共 38 条
[1]  
[Anonymous], 2013, MODERN FLUOROORGANIC
[2]   Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers [J].
Belanger, Etienne ;
Cantin, Katy ;
Messe, Olivier ;
Tremblay, Melanie ;
Paquin, Jean-Francois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1034-1035
[3]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[4]   PREPARATION OF ALPHA-FLUORO-GAMMA-AMINOACIDS [J].
BUCHANAN, RL ;
PATTISON, FL .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (12) :3466-&
[5]  
Chu C. K., 1996, Q U.S. Patent, Patent No. [5,587,362, 5587362]
[6]  
Cox JM, 1997, PESTIC SCI, V50, P297, DOI 10.1002/(SICI)1096-9063(199708)50:4<297::AID-PS592>3.0.CO
[7]  
2-2
[8]   Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation [J].
Fukuzumi, Takeo ;
Shibata, Norio ;
Sugiura, Masayoshi ;
Yasui, Hiroyuki ;
Nakamura, Shuichi ;
Toru, Takeshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4973-4977
[9]   Catalysis for fluorination and trifluoromethylation [J].
Furuya, Takeru ;
Kamlet, Adam S. ;
Ritter, Tobias .
NATURE, 2011, 473 (7348) :470-477
[10]   Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes [J].
Goehler, Sabrina ;
Stark, Christian B. W. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (10) :1605-1614