Catalytic asymmetric synthesis of cyclic α-allylated α-fluoroketones

被引:52
作者
Burger, E. C. [1 ]
Barron, B. R. [1 ]
Tunge, J. A. [1 ]
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
关键词
fluorine; enolate; decarboxylation; palladium;
D O I
10.1055/s-2006-950265
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This manuscript details the development of an asymmetric, palladium-catalyzed, decarboxylative coupling of fluoroenolates with allyl electrophiles.
引用
收藏
页码:2824 / 2826
页数:3
相关论文
共 34 条
[1]   Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions [J].
Arai, S ;
Oku, M ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON LETTERS, 1999, 40 (37) :6785-6789
[2]   1-ALKYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS - A NOVEL FAMILY OF ELECTROPHILIC FLUORINATING AGENTS [J].
BANKS, RE ;
MOHIALDINKHAFFAF, SN ;
LAL, GS ;
SHARIF, I ;
SYVRET, RG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (08) :595-596
[3]   Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[4]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[5]   Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].
Bernardi, L ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326
[6]   Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].
Burger, EC ;
Tunge, JA .
ORGANIC LETTERS, 2004, 6 (22) :4113-4115
[7]   Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4) [J].
Cahard, D ;
Audouard, C ;
Plaquevent, JC ;
Roques, N .
ORGANIC LETTERS, 2000, 2 (23) :3699-3701
[8]   Asymmetric fluorination of enolates with nonracemic N-fluoro-2,10-camphorsultams [J].
Davis, FA ;
Zhou, P ;
Murphy, CK ;
Sundarababu, G ;
Qi, HY ;
Han, W ;
Przeslawski, RM ;
Chen, BC ;
Carroll, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2273-2280
[9]   ASYMMETRIC FLUORINATION OF ENOLATES WITH N-FLUORO 2,10-(3,3-DICHLOROCAMPHORSULTAM) [J].
DAVIS, FA ;
ZHOU, P ;
MURPHY, CK .
TETRAHEDRON LETTERS, 1993, 34 (25) :3971-3974
[10]   Direct organocatalytic α-fluorination of aldehydes and ketones [J].
Enders, D ;
Hüttl, MRM .
SYNLETT, 2005, (06) :991-993