Catalytic enantioselective fluorination of α-cyano acetates catalyzed by chiral palladium complexes

被引：115

作者：

Kim, HR ^{[1
]}

Kim, DY ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Chungnam 336600, South Korea

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 17期

关键词：

chiral palladium complexes; fluorination; asymmetric reactions;

D O I：

10.1016/j.tetlet.2005.02.164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective electrophilic fluorination promoted chiral palladium complexes is described. Treatment of alpha-cyano acetates with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding alpha-cyano alpha-fluoro acetates in high yields with excellent enantiomeric excesses (85-99% ee). (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3115 / 3117

页数：3

共 27 条

[1] Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters
Frantz, R
Hintermann, L
Perseghini, M
Broggini, D
Togni, A
[J]. ORGANIC LETTERS, 2003, 5 (10) : 1709 - 1712
[2] An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters
Fujiwara, T
Sasaki, M
Omata, K
Kabuto, C
Kabuto, K
Takeuchi, Y
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (03) : 555 - 563
[3] An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes
Hamashima, Y
Yagi, K
Takano, H
Tamás, L
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14530 - 14531
[4] Hintermann L, 2000, ANGEW CHEM INT EDIT, V39, P4359, DOI 10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO
[5] 2-P
[6] Hudlicky M., 1995, CHEM ORGANIC FLUORIN, V1st
[7] Enantioselective halogenation reactions
Ibrahim, H
Togni, A
[J]. CHEMICAL COMMUNICATIONS, 2004, (10) : 1147 - 1155
[8] Catalytic enantioselective fluorination of β-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts
Kim, DY
Park, EJ
[J]. ORGANIC LETTERS, 2002, 4 (04) : 545 - 547
[9] Electrophilic NF fluorinating agents
Lal, GS
Pez, GP
Syvret, RG
[J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1737 - 1755
[10] Dicationic [(BINAP)Pd(solvent)2]2+[TfO-]2:: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinones
Li, KL
Hii, KK
[J]. CHEMICAL COMMUNICATIONS, 2003, (10) : 1132 - 1133

← 1 2 3 →