Catalytic enantioselective fluorination and amination of β-keto phosphonates catalyzed by chiral palladium complexes

被引:163
作者
Kim, SM [1 ]
Kim, HR [1 ]
Kim, DY [1 ]
机构
[1] Soonchunhyang Univ, Div Appl Sci, Dept Chem, Asan 336745, Chungnam, South Korea
关键词
D O I
10.1021/ol050413a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic enantioselective fluorination and amination of beta-keto phosphonates catalyzed by chiral palladium complexes is described. Treatment of beta-keto phosphonates with N-fluorobenzenesulfonimide (NFSI) as electrophilic fluorinating reagent and diethyl azodicarboxylate (DEAD) as electrophilic amination reagent under mild reaction conditions afforded the corresponding alpha-substituted beta-keto phosphonates in moderate to excellent yields with excellent enantiomeric excesses.
引用
收藏
页码:2309 / 2311
页数:3
相关论文
共 41 条
[1]   (α-monofluoroalkyl)phosphonates:: a class of isoacidic and "tunable" mimics of biological phosphates [J].
Berkowitz, DB ;
Bose, M .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (01) :13-33
[2]   α-fluorinated phosphonates as substrate mimics for glucose 6-phosphate dehydrogenase:: the CHF stereochemistry matters [J].
Berkowitz, DB ;
Bose, M ;
Pfannenstiel, TJ ;
Doukov, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4498-4508
[3]   An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates [J].
Bernardi, L ;
Zhuang, W ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5772-5773
[4]   Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].
Bernardi, L ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326
[5]  
BLACKBURN GM, 1981, CHEM IND-LONDON, P134
[6]   OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].
DHAWAN, B ;
REDMORE, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144
[7]   Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis [J].
France, S ;
Weatherwax, A ;
Lectka, T .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) :475-479
[8]   Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex [J].
Fujii, A ;
Hagiwara, E ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5450-5458
[9]   Nuclear magnetic resonance and restrained molecular dynamics studies of the interaction of an epidermal growth factor-derived peptide with protein tyrosine phosphatase 1B [J].
Glover, NR ;
Tracey, AS .
BIOCHEMISTRY, 1999, 38 (16) :5256-5271
[10]  
Gröger H, 2000, CHEM-EUR J, V6, P943