Ready Synthetic Access to Enantiopure Allylic α(F)-Branched Fluoroalkenes

被引:19
作者
Larnaud, Florent [1 ,2 ,3 ]
Malassis, Julien [1 ,2 ,3 ]
Pfund, Emmanuel [1 ,2 ]
Linclau, Bruno [3 ]
Lequeux, Thierry [1 ,2 ]
机构
[1] Univ Caen Basse Normandie, UMR CNRS 6507, Lab Chim Mol & Thioorgan, F-14050 Caen, France
[2] Univ Caen Basse Normandie, FR3038, ENSICAEN, F-14050 Caen, France
[3] Univ Southampton, Southampton SO17 1BJ, Hants, England
关键词
NUCLEOPHILIC FLUOROALKYLATION; CHEMISTRY; FLUORINE;
D O I
10.1021/ol400917j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convenient access to homochiral fluoroalkenes is described via a Julia-Kocienski olefination reaction. The required homochiral fluorosulfone is synthesized by a Mitsunobu reaction from readily available enantiopure secondary alcohols.
引用
收藏
页码:2450 / 2453
页数:4
相关论文
共 33 条
[1]   Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction [J].
Aissa, Christophe .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) :1831-1844
[2]   Synthesis and biological evaluation of γ-fluoro-β, γ-unsaturated acids [J].
Asakura, Noriaki ;
Usuki, Yoshinosuke ;
Iio, Hideo ;
Tanaka, Toshio .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (06) :800-808
[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]   Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase [J].
Burkhart, JP ;
Weintraub, PM ;
Gates, CA ;
Resvick, RJ ;
Vaz, RJ ;
Friedrich, D ;
Angelastro, MR ;
Bey, P ;
Peet, NP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :929-934
[5]   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
[6]   A convenient one-step synthesis of fluoroethylidene derivatives [J].
Chevrie, D ;
Lequeux, T ;
Demoute, JP ;
Pazenok, S .
TETRAHEDRON LETTERS, 2003, 44 (44) :8127-8130
[7]   An Evaluation of Peptide-Bond Isosteres [J].
Choudhary, Amit ;
Raines, Ronald T. .
CHEMBIOCHEM, 2011, 12 (12) :1801-1807
[8]   Chiral dipeptide mimics possessing fluoroolefin moiety: a relevant tool for conformational and medicinal studies [J].
Couve-Bonnaire, Samuel ;
Cahard, Dominique ;
Pannecoucke, Xavier .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (08) :1151-1157
[9]   Vinyl fluoride as an isoelectronic replacement for an enolate anion: Inhibition of type II dehydroquinases [J].
Frederickson, M ;
Coggins, JR ;
Abell, C .
CHEMICAL COMMUNICATIONS, 2002, (17) :1886-1887
[10]   Fluorinated 1-Phenyl-1H-tetrazol-5-yl Sulfone Derivatives as General Reagents for Fluoroalkylidene Synthesis [J].
Ghosh, Arun K. ;
Zajc, Barbara .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8531-8540