An Efficient and Highly Selective Synthesis of (Z)-Fluoroenol Phosphates from Hydroxy Difluorophosphonates

被引：16

作者：

Beier, Petr ^{[1
]}

Pohl, Radek ^{[1
]}

Alexandrova, Anastasia V. ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

SYNTHESIS-STUTTGART | 2009年 / 06期

关键词：

phosphonates; phosphates; rearrangements; eliminations; enols; ENOL PHOSPHATES; PERKOW REACTION; KETONES; FLUORINE; PHOSPHITES; ALDEHYDES; CHLORIDES; REAGENTS; MOIETY; ROUTE;

D O I：

10.1055/s-0028-1087803

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted 2-aryl-2-hydroxy-1,1-difluorophosphonates undergo a reaction with potassium tert-butoxide to provide selectively (Z)-2-fluoro-1-arylvinyl phosphates in high yields.

引用

页码：957 / 962

页数：6

共 37 条

[1] Diastereoselective vinyl phosphate/beta-keto phosphonate rearrangements
An, JG
Wilson, JM
An, YZ
Wiemer, DF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) : 4040 - 4045
[2] Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate
Beier, Petr
Alexandrova, Anastasia V.
Zibinsky, Mikhail
Prakash, G. K. Surya
[J]. TETRAHEDRON, 2008, 64 (49) : 10977 - 10985
[3] BERGMANN ED, 1960, J CHEM SOC, P462
[4] Fluorine in medicinal chemistry
Böhm, HJ
Banner, D
Bendels, S
Kansy, M
Kuhn, B
Müller, K
Obst-Sander, U
Stahl, M
[J]. CHEMBIOCHEM, 2004, 5 (05) : 637 - 643
[5] PHOSPHORUS TRICHLORIDE-OXYGEN-OLEFIN REACTION - CONFORMATION AND ELIMINATION STUDIES ON PRODUCTS DERIVED FROM 1-CHLORO-2-FLUORO-ETHYLENE AND 1,2-DIFLUORO-ETHYLENE
BOYCE, CBC
WEBB, SB
PHILLIPS, L
AGER, IR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (14): : 1644 - 1650
[6] Addition of trifluoromethyltrimethylsilane to acyl phosphonates: Synthesis of TMS-Protected 1-alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-aryldifluoroethenyl phosphates
Demir, Ayhan S.
Eymur, Serkan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) : 8527 - 8530
[7] The high stereoselective synthesis of β-alkynyl-enol phosphates
Ding, YX
Huang, XG
[J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (03) : 449 - 454
[8] A new synthesis of enol phosphates
Ding, YX
Wang, WH
Liu, ZF
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 118 : 113 - 116
[9] REACTION OF F-ALKANOIC ACID-CHLORIDES WITH TRIALKYL PHOSPHITES LEADING TO 1-(DIALKOXYPHOSPHINYL)OXY-F-1-ALKENEPHOSPHONATES OR 1-(DIALKOXYPHOSPHINYL)OXY-1H-F-ALKANEPHOSPHONATES
ISHIHARA, T
MAEKAWA, T
YAMASAKI, Y
ANDO, T
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1987, 34 (3-4) : 323 - 335
[10] NOVEL SYNTHESIS OF F-1-ALKENE-1-PHOSPHONATE DERIVATIVES FROM F-ALKANOYL CHLORIDES AND THEIR EFFICIENT USE FOR PREPARING FLUORO-ALPHA,BETA-ENONES
ISHIHARA, T
MAEKAWA, T
ANDO, T
[J]. TETRAHEDRON LETTERS, 1983, 24 (39) : 4229 - 4232

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