A practical route for the highly stereoselective synthesis of tetrasubstituted fluoroalkenes

被引:16
作者
Cao, Chun-Ru [1 ]
Ou, Song [1 ]
Jiang, Min [1 ]
Liu, Jin-Tao [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGH-YIELD SYNTHESIS; JULIA OLEFINATION; WEINREB AMIDES; FLUORO; PHARMACEUTICALS; EFFICIENT; SULFONES; ALKENES; ESTERS; MILD;
D O I
10.1039/c3ob42093k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of tetrasubstituted fluoroatkene derivatives were synthesized by the reaction of alpha-fluoro-beta-carbonyl benzothiazol-2-yl sulfones with various nucleophiles in good yields with high stereoselectivities. The predominant cis configuration of fluorine and alkynyl groups was observed. A single isomer was obtained when a ketone, acetate or amide was used as the substrate in the presence of a base.
引用
收藏
页码:467 / 473
页数:7
相关论文
共 41 条
[1]   Novel Aromatic Fluoroolefins via Fluoro-Julia-Kocienski Olefination [J].
Allendoerfer, Nadine ;
Es-Sayed, Mazen ;
Nieger, Martin ;
Braese, Stefan .
SYNTHESIS-STUTTGART, 2010, (20) :3439-3448
[2]   Highly efficient and stereoselective Julia-Kocienski protocol for the synthesis of α-fluoro-α,β-unsaturated esters and Weinreb amides employing 3,5-bis(trifluoromethyl)phenyl (BTFP) sulfones [J].
Alonso, Diego A. ;
Fuensanta, Monica ;
Gomez-Bengoa, Enrique ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) :1823-1829
[3]   Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].
Begue, Jean-Pierre ;
Bonnet-Delpon, Daniele .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012
[4]   FLUOROOLEFIN PEPTIDE ISOSTERES - TOOLS FOR CONTROLLING PEPTIDE CONFORMATIONS [J].
BOROS, LG ;
DECORTE, B ;
GIMI, RH ;
WELCH, JT ;
WU, Y ;
HANDSCHUMACHER, RE .
TETRAHEDRON LETTERS, 1994, 35 (33) :6033-6036
[5]   Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].
Bouchy, A ;
Rinaldi, D ;
Rivail, JL .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281
[6]   Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones [J].
Calata, Charlene ;
Pfund, Emmanuel ;
Lequeux, Thierry .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9399-9405
[7]   Scope and limitations of the Julia-Kocienski reaction with fluorinated sulfonylesters [J].
Calata, Charlene ;
Catel, Jean-Marie ;
Pfund, Emmanuel ;
Lequeux, Thierry .
TETRAHEDRON, 2009, 65 (20) :3967-3973
[8]   A convenient one-step synthesis of fluoroethylidene derivatives [J].
Chevrie, D ;
Lequeux, T ;
Demoute, JP ;
Pazenok, S .
TETRAHEDRON LETTERS, 2003, 44 (44) :8127-8130
[9]   A Convergent, Unified Approach to Functionalized Fluoro- and Trifluoromethyl Alkenes [J].
Debien, Laurent ;
Quiclet-Sire, Beatrice ;
Zard, Samir S. .
ORGANIC LETTERS, 2012, 14 (19) :5118-5121
[10]   Fluoro-Julia Olefination as a Mild, High-Yielding Route to α-Fluoro Acrylonitriles [J].
del Solar, Maria ;
Ghosh, Arun K. ;
Zajc, Barbara .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8206-8211