Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids

被引：110

作者：

Bernardi, L ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 10期

关键词：

D O I：

10.1039/b415568h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct chiral Lewis acidic enantioselective chlorination and fluorination of beta-keto phosphonates is presented; the chlorination proceeds in high yields and with up to 94% ee using NCS as the chloro source, while the fluorination with (PhSO2)(2)NF (NFSI) gives the optically active alpha-fluoro-beta-keto phosphonates in moderate to good yields and with up to 91% ee.

引用

页码：1324 / 1326

页数：3

共 42 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[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]

BLACKBURN GM, 1981, CHEM IND-LONDON, P134

[4] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[5] Fluorinated ylides and related compounds [J].

Burton, DJ ;

Yang, ZY ;

Qiu, WM .

CHEMICAL REVIEWS, 1996, 96 (05) :1641-1715

[6] WHY IS PHOSPHONODIFLUOROMETHYL PHENYLALANINE A MORE POTENT INHIBITORY MOIETY THAN PHOSPHONOMETHYL PHENYLALANINE TOWARD PROTEIN-TYROSINE PHOSPHATASES [J].

CHEN, L ;

WU, L ;

OTAKA, A ;

SMYTH, MS ;

ROLLER, PP ;

BURKE, TR ;

DENHERTOG, J ;

ZHANG, ZY .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 216 (03) :976-984

[7] Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts [J].

Desimoni, G ;

Faita, G ;

Quadrelli, P .

CHEMICAL REVIEWS, 2003, 103 (08) :3119-3154

[8] Organic fluorine hardly ever accepts hydrogen bonds [J].

Dunitz, JD ;

Taylor, R .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (01) :89-98

[9] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].

ENGEL, R .

CHEMICAL REVIEWS, 1977, 77 (03) :349-367

[10] Catalytic, asymmetric α-chlorination of acid halides [J].

France, S ;

Wack, H ;

Taggi, AE ;

Hafez, AM ;

Wagerle, TR ;

Shah, MH ;

Dusich, CL ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4245-4255

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