Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

被引：17

作者：

Ayoup, Mohammed Salah ^{[1
,2
]}

Cordes, David B. ^{[1
]}

Slawin, Alexandra M. Z. ^{[1
]}

O'Hagan, David ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷

基金：

英国工程与自然科学研究理事会;

关键词：

cyclohexane carbonylation; fluorine containing building blocks: organofluorine chemistry; AMINO-ACIDS; INHIBITORS; REDUCTION; MOTIF;

D O I：

10.3762/bjoc.11.287

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium catalysed carbonylation reactions using the meta-and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

引用

页码：2671 / 2676

页数：6

共 19 条

[1] A regio- and stereo-controlled approach to triazoloquinoxalinyl C-nucleosides [J].

Amer, Adel ;

Ayoup, Mohammed Salah ;

Khattab, Sherine Nabil ;

Hassan, Seham Yassen ;

Langer, Vratislav ;

Senior, Samir ;

El Massry, Abdel Moneim .

CARBOHYDRATE RESEARCH, 2010, 345 (17) :2474-2484

[2] Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif [J].

Ayoup, Mohammed Salah ;

Cordes, David B. ;

Slawin, Alexandra M. Z. ;

O'Hagan, David .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (20) :5621-5624

[3] PALLADIUM-CATALYZED FORMYLATION OF ORGANIC HALIDES WITH CARBON-MONOXIDE AND TIN HYDRIDE [J].

BAILLARGEON, VP ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :452-461

[4] Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids [J].

Barfoot, CW ;

Harvey, JE ;

Kenworthy, MN ;

Kilburn, JP ;

Ahmed, M ;

Taylor, RJK .

TETRAHEDRON, 2005, 61 (13) :3403-3417

[5] Design, modelling, synthesis and biological evaluation of peptidomimetic phosphinates as inhibitors of matrix metalloproteinases MMP-2 and MMP-8 [J].

Bianchini, G ;

Aschi, M ;

Cavicchio, G ;

Crucianelli, M ;

Preziuso, S ;

Gallina, C ;

Nastari, A ;

Gavuzzo, E ;

Mazza, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) :4740-4749

[6] Phosphoramidite accelerated copper(I)-catalyzed [3+2] cycloadditions of azides and alkynes [J].

Campbell-Verduyn, Lachlan S. ;

Mirfeizi, Leila ;

Dierckx, Rudi A. ;

Elsinga, Philip H. ;

Feringa, Ben L. .

CHEMICAL COMMUNICATIONS, 2009, (16) :2139-2141

[7] Stepwise Preparation of All-cis 1,3,4-Trifluoro-2-phenylcyclohexane, Avoiding a Phenonium Intermediate [J].

Durie, Alastair J. ;

Fujiwara, Tomoya ;

Al-Maharik, Nawaf ;

Slawin, Alexandra M. Z. ;

O'Hagan, David .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8228-8233

[8] Synthesis and Elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: A Polar Cyclohexane Motif [J].

Durie, Alastair J. ;

Fujiwara, Tomoya ;

Cormanich, Rodrigo ;

Buehl, Michael ;

Slawin, Alexandra M. Z. ;

O'Hagan, David .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (21) :6259-6263

[9] Fluorocyclohexanes: synthesis and structure of all-syn-1,2,4,5-tetrafluorocyclohexane [J].

Durie, Alastair J. ;

Slawin, Alexandra M. Z. ;

Lebl, Tomas ;

Kirsch, Peer ;

O'Hagan, David .

CHEMICAL COMMUNICATIONS, 2012, 48 (77) :9643-9645

[10] Synthesis and structure of all-syn-1,2,3,4-tetrafluorocyclohexane [J].

Durie, Alastair J. ;

Slawin, Alexandra M. Z. ;

Lebl, Tomas ;

Kirschb, Peer ;

O'Hagan, David .

CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8265-8267

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