Summary.
α-Trifluoromethyl α-amino acids with unsaturated side-chains have been prepared from 5-fluoro-4-trifluoromethyloxazole and allyl, propargyl as well as terpene alcohols in a one-pot procedure.
Similar content being viewed by others
Abbreviations
- Tfm Gly:
-
Trifluoromethylglycine
- Mag:
-
Methylallylglycine
- Tfmag:
-
Trifluoromethylallyl-glycine
References
A Aubry G Boussard MT Cung M Marraud B Vitoux (1988) ArticleTitleModifications of the β-turn conformation in the peptide and pseudopeptide series (review) J Chim Phys PCB 85 345–359 Occurrence Handle1:CAS:528:DyaL1cXktFyqs7c%3D
R Badorrey C Cativiela MD Diaz-De-Villegas JA Galvez Y Lapena (1997) ArticleTitleA new approach to the stereoselective synthesis of conveniently protected α-allyl substituted amino acids; chiral key compounds in the synthesis of constrained peptide isostere constituents Tetrahedron Asymm 8 311–317 Occurrence Handle1:CAS:528:DyaK2sXhtFCks70%3D Occurrence Handle10.1016/S0957-4166(96)00516-2
HE Blackwell RH Grubbs (1998) ArticleTitleHighly efficient synthesis of covalently cross-linked peptide helices by ring-closing metathesis Angew Chem Int Ed 37 3281–3284 Occurrence Handle1:CAS:528:DyaK1MXksVehtA%3D%3D Occurrence Handle10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO;2-V
QB Broxterman B Kaptein J Kamphuis HE Schoemaker (1992) ArticleTitleSynthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids J Org Chem 57 6286–6294 Occurrence Handle1:CAS:528:DyaK38XmtlCntbY%3D Occurrence Handle10.1021/jo00049a041
K Burger R Ottlinger H Goth J Firl (1982) ArticleTitleReaction behavior of trifluoromethyl groups. Synthesis of 1,3-azoles from trifluoromethyl substituted hetero-1,3-dienes Chem Berl 115 2494–2507 Occurrence Handle1:CAS:528:DyaL38XlsVCrs7c%3D
Burger K, Geith K, Huebl D (1988a) A new method for regioselective introduction of trifluoromethyl groups into heteroarenes. Part 1. Synthesis of trifluoromethyl substituted 1,3-azoles (oxazoles, thiazoles, imidazoles). Synthesis, 189–194
Burger K, Hübl D, Geith K (1988b) A new method for regioselective introduction of trifluoromethyl groups into heteroarenes. Part 2. Nucleophilic substitution of 5-fluoro-4-trifluoromethyl-1,3-azoles. Synthesis, 194–198
K Burger K Gaa K Geith (1988c) ArticleTitleSynthesis of trifluoromethyl substituted aspartic acid and some of its derivatives J Fluorine Chem 41 429–433 Occurrence Handle1:CAS:528:DyaL1MXhvFegt7c%3D Occurrence Handle10.1016/S0022-1139(00)81044-1
K Burger K Geith K Gaa (1988d) ArticleTitleA preparatively simple access to 2-substituted 3,3,3-trifluoroalanine derivatives Angew Chem Int Ed 27 848 Occurrence Handle10.1002/anie.198808481
Burger K, Höß E, Geith K (1990a) 5-Amino-4-(trifluoromethyl)thiazoles and 5-aminomethyl-4-trifluoromethyl-1,3-azoles: Useful starting materials for the synthesis of biologically active compounds. Synthesis, 360–365
K Burger K Geith N Sewald (1990b) ArticleTitleSynthetic potential of trifluoromethyl substituted tin heterocycles J Fluorine Chem 46 105–122 Occurrence Handle1:CAS:528:DyaK3cXhvFylsrg%3D Occurrence Handle10.1016/S0022-1139(00)81563-8
K Burger K Gaa (1990) ArticleTitleAn efficient synthesis for α-trifluoromethyl substituted ω-carboxy-α-amino acids Chem-Ztg 114 101–104 Occurrence Handle1:CAS:528:DyaK3cXltlakt7w%3D
K Burger K Gaa K Mütze (1991a) ArticleTitleIntroduction of carbocyclic and heterocyclic units into the side chain of α-trifluoromethyl substituted α-amino acids via Diels-Alder reaction Chem-Ztg 115 292–295 Occurrence Handle1:CAS:528:DyaK38XosVWhug%3D%3D
K Burger K Gaa K Mütze (1991b) ArticleTitleSynthesis of trifluoromethyl-substituted ω-phosphinoyl-amino acids Chem-Ztg 115 328–330 Occurrence Handle1:CAS:528:DyaK38Xht12msLk%3D
K Burger A Fuchs L Hennig B Helmreich (2001) ArticleTitleLow temperature domino reactions. A ready access to trifluoromethyl substituted butenolides and their thioanalogues Tetrahedron Lett 42 1657–1659 Occurrence Handle1:CAS:528:DC%2BD3MXht1yrtLk%3D Occurrence Handle10.1016/S0040-4039(01)00013-2
K Burger L Hennig A Fuchs D Greif J Spengler F Albericio (2005) ArticleTitleDomino reactions with fluorinated five-membered heterocycles. Synthesis of trifluoromethyl substituted butenolides and γ-keto acids Mh Chemie 136 1763–1779 Occurrence Handle1:CAS:528:DC%2BD2MXhtVGntrbM
HL Carrell JP Glusker EA Piercy WC Stallings DE Zacharias RL Davis C Astbury CHL Kennard (1987) ArticleTitleMetal chelation versus internal hydrogen bonding of the α-hydroxy carboxylate group J Am Chem Soc 109 8067–8071 Occurrence Handle1:CAS:528:DyaL2sXmtlGksL4%3D Occurrence Handle10.1021/ja00260a019
N Engel B Kuebel W Steglich (1977) ArticleTitleCarbon-carbon bonding of carboxylic acids with allyl alcohols using 2-phenylglycine as vehicle Angew Chem Int Ed 16 394–396
R Filler Y Kobayashi (Eds) (1982) Biomedicinal aspects of fluorine chemistry Elsevier Biomedical Amsterdam
J Fischer C Kilpert U Klein W Steglich (1986) ArticleTitleStereochemistry of [3.3]-sigmatropic rearrangements in the oxazole series Tetrahedron 42 2063–2074 Occurrence Handle1:CAS:528:DyaL2sXhtVaisbo%3D Occurrence Handle10.1016/S0040-4020(01)87623-7
JJ Gajewski (1997) ArticleTitleThe Claisen rearrangement. Response to solvents and substituents: the case of both hydrophobic and hydrogen bond acceleration in water and for a variable transition state Acc Chem Res 30 219–225 Occurrence Handle1:CAS:528:DyaK2sXislKhu7Y%3D Occurrence Handle10.1021/ar9600493
SH Gellman (1998) ArticleTitleFoldamers. A manifesto Acc Chem Res 31 173–180 Occurrence Handle1:CAS:528:DyaK1cXhvF2qtr0%3D Occurrence Handle10.1021/ar960298r
JT Gerig (1994) ArticleTitleFluorine NMR of proteins Prog Magn Reson Spectrosc 26 293–370 Occurrence Handle1:CAS:528:DyaK2cXktVCit7c%3D Occurrence Handle10.1016/0079-6565(94)80009-X
A Giannis T Kolter (1993) ArticleTitlePeptide mimetics for receptor ligands: discovery, development, and medicinal perspectives Angew Chem Int Ed 32 1244–1267 Occurrence Handle10.1002/anie.199312441
Groth U, Schöllkopf U, (1983) Asymmetric syntheses via heterocyclic intermediates; XIX. On the enantioselective synthesis of β-fluorovaline methyl ester and related α-amino-β-fluorocarboxylic esters. Synthesis, 673–675
RM Guinn AO Margot JR Taylor M Schumacher DS Clark HW Blanch (1995) ArticleTitleSynthesis and characterization of polyamides containing unnatural amino acids Biopolymers 35 503–512 Occurrence Handle7766820 Occurrence Handle1:CAS:528:DyaK2MXltVKqurY%3D Occurrence Handle10.1002/bip.360350509
VJ Hruby (1982) ArticleTitleConformational restrictions of biologically active peptides via amino acid side chain groups Life Sci 31 189–199 Occurrence Handle6126794 Occurrence Handle1:CAS:528:DyaL38Xks1Kns7k%3D Occurrence Handle10.1016/0024-3205(82)90578-1
VJ Hruby F al-Obeidi W Kazmierski (1990) ArticleTitleEmerging approaches in the molecular design of receptor-selective peptide ligands: conformational, topographical and dynamic considerations Biochem J 268 249–262 Occurrence Handle2163604 Occurrence Handle1:CAS:528:DyaK3cXktFOqs7Y%3D
Jaeckel C, Koksch B (2005) Fluorine in peptide design and engineering. Eur J Org Chem 4483–4503
B Kaptein WHJ Boesten QB Broxterman HE Schoemaker J Kamphuis (1992) ArticleTitleSynthesis of α,α-disubstituted α-amino acid amides by phase-transfer catalyzed alkylation Tetrahedron Lett 33 6007–6010 Occurrence Handle1:CAS:528:DyaK3sXjvFemsA%3D%3D Occurrence Handle10.1016/S0040-4039(00)61112-7
B Kaptein WHJ Boesten QB Broxterman PJH Peters HE Schoemaker J Kamphuis (1993) ArticleTitleEnzymatic resolution of α,α-disubstituted α-amino acid esters and amides Tetrahedron Asymmetry 4 1113–1116 Occurrence Handle1:CAS:528:DyaK2cXhtlGjur0%3D Occurrence Handle10.1016/S0957-4166(00)80217-7
IL Karle P Balaram (1990) ArticleTitleStructural characteristics of α-helical peptide molecules containing Aib residues Biochemistry 29 6747–6756 Occurrence Handle2204420 Occurrence Handle1:CAS:528:DyaK3cXksFCnsr4%3D Occurrence Handle10.1021/bi00481a001
B Koksch N Sewald HJ Hofmann K Burger HD Jakubke (1997) ArticleTitleProteolytically stable peptides by incorporation of αTfm amino acids J Pept Sci 3 157–167 Occurrence Handle9230481 Occurrence Handle1:CAS:528:DyaK2sXktlaqsro%3D Occurrence Handle10.1002/(SICI)1099-1387(199705)3:3<157::AID-PSC94>3.0.CO;2-W
Koksch B, Jakubke H-D, Wenschuh H, Dietmeier K, Starostin A, Wooley A, Dathe M, Müller G, Gußmann M, Hoffmann HJ, Michel T, Burger K (1999) In: Bajusz S, Hudecz F (eds) Peptides: Proceedings of the Twenty-Fifth European Peptide Symposium, Académiai Kiadó, Budapest, p 670
B Kübel G Hoefle W Steglich (1975) ArticleTitleHetero Cope rearrangement in the cyclization of N-acyl amino acid allyl and propargyl esters in 5-oxazolinones Angew Chem Int Ed 14 58–60 Occurrence Handle10.1002/anie.197500581
VP Kukhar VA Soloshonok (1995) Fluorine-containing amino acids SeriesTitleSynthesis and properties Wiley New York
GR Marshall JD Clark JB Dunbar SuffixJr GD Smith J Zabrocki AS Redlinski MT Leplawy (1988) ArticleTitleConformational effects of chiral α,α-dialkyl amino acids. I. C-Terminal tetrapeptides of emerimicin containing α-ethylalanine Int J Pept Protein Res 32 544–555 Occurrence Handle3246479 Occurrence Handle1:CAS:528:DyaL1MXlvFGgurw%3D Occurrence Handle10.1111/j.1399-3011.1988.tb01386.x
T Nagai G Nishioka M Koyama A Ando T Miki I Kumadaki (1992) ArticleTitleReactions of trifluoromethyl ketones. IX. Investigation of the steric effect of a trifluoromethyl group based on the stereochemistry of dehydration of trifluoromethyl homoallyl alcohols J Fluorine Chem 57 229–237 Occurrence Handle1:CAS:528:DyaK3sXmsF2m Occurrence Handle10.1016/S0022-1139(00)82835-3
C Peggion R Flammengo E Mossel QB Broxterman B Kaptein J Kamphuis F Formaggio M Crisma C Toniolo (2000) ArticleTitleMag: a Cα-methylated, side-chain unsaturated α-amino acid. Introduction into model peptides and conformational preference Tetrahedron 56 3589–3601 Occurrence Handle1:CAS:528:DC%2BD3cXjvFOquro%3D Occurrence Handle10.1016/S0040-4020(00)00274-X
DS Poche SJ Thibodeaux VC Rucker IM Warner WH Daly (1997) ArticleTitleSynthesis of novel γ-alkenyl L-glutamate derivatives containing a terminal CC double bond to produce polypeptides with pendant unsaturation Macromolecules 30 8081–8084 Occurrence Handle1:CAS:528:DyaK2sXnsVSkt70%3D Occurrence Handle10.1021/ma970703+
A Polese F Formaggio M Crisma G Valle C Toniolo GM Bonora QB Broxterman J Kamphuis (1996) ArticleTitleLinear oligopeptides. Peptide helixes as rigid molecular rules: a conformational study of isotactic homopeptides from α-methyl-α-isopropylglycine, [L-(αMe)Val]n Chem Eur J 2 1104–1111 Occurrence Handle1:CAS:528:DyaK28XlvFOqsbs%3D
Rutjes FPJT, Veerman JJN, Meester WJN, Hiemstra H, Schoemaker HE (1999) Synthesis of enantiopure, functionalized pipecolic acids via amino acid-derived N-acyliminium ions. Eur J Org Chem, 1127–1135
HE Schoemaker WHJ Boesten B Kaptein HFM Hermes T Sonke QB Broxterman WJJ Van den Tweel J Kamphuis (1992) ArticleTitleChemo-enzymatic synthesis of amino acids and derivatives Pure Appl Chem 64 1171–1175 Occurrence Handle1:CAS:528:DyaK38XlvFahtLY%3D
D Seebach (1990) ArticleTitleOrganic synthesis – where next? Angew Chem Int Ed 29 1320–1367 Occurrence Handle10.1002/anie.199013201
JE Semple NK Minami SY Tamura TK Brunck RF Nutt WC Ripka (1997) ArticleTitleRational design and synthesis of a novel, selective class of thrombin inhibitors: P1-argininal derivatives incorporating P3–P4 quaternary lactam dipeptide surrogates Bioorg Med Chem Lett 7 2421–2426 Occurrence Handle1:CAS:528:DyaK2sXmvVKgtLg%3D Occurrence Handle10.1016/S0960-894X(97)00446-0
N Sewald H-D Jakubke (2000) Peptides: chemistry and biology Wiley-VCH Weinheim
AF Spatola (1983) NoChapterTitle B Weinstein (Eds) Chemistry and biochemistry of amino acids, peptides and proteins NumberInSeries7 Dekker New York 267–357
C Toniolo E Benedetti (1991) ArticleTitleStructures of polypeptides from α-amino acids disubstituted at the α-carbon Macromolecules 24 4004–4009 Occurrence Handle1:CAS:528:DyaK3MXkt12rt7w%3D Occurrence Handle10.1021/ma00014a006
C Toniolo M Crisma F Formaggio G Valle G Cavicchioni G Precigoux A Aubry J Kamphuis (1993) ArticleTitleStructures of peptides from α-amino acids methylated at the α-carbon Biopolymers 33 1061–1072 Occurrence Handle8343585 Occurrence Handle1:CAS:528:DyaK3sXmtVersLk%3D Occurrence Handle10.1002/bip.360330708
A van der Werf RM Kellogg (1988) ArticleTitleSynthesis of α-allyl-α-amino acids by means of a palladium catalyzed intramolecular rearrangement Tetrahedron Lett 29 4981–4984 Occurrence Handle1:CAS:528:DyaL1MXktVOktLk%3D Occurrence Handle10.1016/S0040-4039(00)80658-9
H Waldmann (2003) ArticleTitlePerspective at the crossroads of chemistry and biology Bioorg Med Chem 11 2045–3051 Occurrence Handle10.1016/S0968-0896(03)00266-9 Occurrence Handle1:CAS:528:DC%2BD3sXks1amtrk%3D
JT Welch S Eswarakrishnan (1991) Fluorine in bioorganic chemistry Wiley New York
RM Williams (1999) ArticleTitleAsymmetric syntheses of unnatural amino acids and hydroxyethylene peptide isosteres Methods Mol Med 23 339–356 Occurrence Handle1:CAS:528:DC%2BD3cXptVClug%3D%3D
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Burger, K., Hennig, L., Tsouker, P. et al. Domino reactions with fluorinated five-membered heterocycles. α-Trifluoromethyl α-amino acids with unsaturated side-chains. Amino Acids 31, 427–433 (2006). https://doi.org/10.1007/s00726-006-0321-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-006-0321-2