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2015 | 2 | 1 |
Tytuł artykułu

Synthesis of novel chiral bithiophenebased phosphine oxides as Lewis bases in organocatalytic stereoselective reactions

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Novel enantiomerically pure tetramethylbithiophene diphosphine oxides (tetraMe-BITIOPO) featuring differently substituted aromatic rings at the phosphorous atoms were synthesized, fully characterized and isolated in enantiomerically pure form. The new Lewis bases were tested as organocatalysts in two different reactions involving trichlorosilyl compounds. The introduction of electron donating substituents on the aromatic rings connected to the phosphine oxide groups positively affected the chemical and stereochemical catalytic efficiency of these ligands. The new catalysts were able to promote the allylation of aldehydes with allyltrichlorosilane in up to 76% yield and up to 86% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones in high diastereoselectivity (up to 88:12 anti:syn ratio) and up to 72% ee.
Wydawca

Rocznik
Tom
2
Numer
1
Opis fizyczny
Daty
otrzymano
2014-11-27
zaakceptowano
2015-02-11
online
2015-06-15
Twórcy
autor
  • Dipartimento di Chimica, Universita’ degli Studi di
    Milano, via Golgi 19, 20133 Milano, Italy
  • Dipartimento di Chimica, Universita’ degli Studi di
    Milano, via Golgi 19, 20133 Milano, Italy
  • Dipartimento del Farmaco, Istituto Superiore di Sanità,
    viale Regina Elena 299, 00161 Roma, Italy
  • Dipartimento di Scienza ed Alta Tecnologia
    dell’Università dell’Insubria, via Valleggio, 11, 22100 Como, Italy
Bibliografia
  • [1] Benaglia M., Rossi S., Chiral phosphine oxides in present-dayorganocatalysis, Org. Biomol. Chem., 2010, 8, 3824-3830.
  • [2] Rossi S., Benaglia M., Genoni A., Organic reactions mediatedby tetrachlorosilane, Tetrahedron, 2014, 70, 2065-2080.
  • [3] Simonini V., Benaglia M., Benincori T., A new class of chiralLewis basic metal-free catalysts for stereoselective allylationsof aldehydes, Adv. Synth. Catal., 2008, 350, 561-564;
  • [4] Nakajima M., Kotani S., Ishizuka T., Hashimoto S., Chiralphosphine oxide BINAPO as a catalyst for enantioselectiveallylation of aldehydes with allyltrichlorosilanes, TetrahedronLett., 2005, 46, 157-159.
  • [5] Chen J., Liu D., Fan D., Liu Y., Zhang W., Synthesis of axiallychiral C10-BridgePHOS oxides and their use as organocatalystsin enantioselective allylations of aldehydes, Tetrahedron, 2013,69, 8161-8168.
  • [6] Tokuoka E., Kotani S., Matsunaga H., Ishizuka T., HashimotoS., Nakajima M., Asymmetric ring opening of meso-epoxidescatalyzed by the chiral phosphine oxide BINAPO, Tetrahedron:Asymmetry, 2005, 16, 2391-2392.
  • [7] Kotani S., Furusho H., Sugiura M., Nakajima M., Facilesynthesis of chiral 1,2-chlorohydrins via the ring-openingof meso-epoxides catalyzed by chiral phosphine oxides,Tetrahedron, 2013, 69, 3075-3081.
  • [8] Nakanishi K., Kotani S., Sugiura M., Nakajima M., Firstasymmetric Abramov-type phosphonylation of aldehydeswith trialkyl phosphites catalyzed by chiral Lewis bases,Tetrahedron, 2008, 64, 6415-6419.
  • [9] Ohmaru Y., Sato N., Mizutani M., Kotani S., Sugiura M.,Nakajima M., Synthesis of aryl group-modified DIOP dioxides(Ar-DIOPOs) and their application as modular Lewis basecatalysts, Org. Biomol. Chem., 2012, 10, 4562-4570.
  • [10] Kashiwagi T. Kotani S., Sugiura M., Nakajima M., Synthesisof γ-amino alcohols from aldehydes, enamines, and trichlorosilaneusing Lewis base catalysts, Tetrahedron, 2011, 67,531-539.
  • [11] Sugiura M., Kumahara M., Nakajima M., Asymmetric synthesisof 4H-1,3-oxazines: enantioselective reductive cyclization ofN-acylated β-amino enones with trichlorosilane catalyzed bychiral Lewis bases, Chem Commun., 2009, 3585-3587.
  • [12] Kotani S., Hashimoto, S., Nakajima M., Chiral phosphine oxideBINAPO as a Lewis base catalyst for asymmetric allylation and aldol reaction of trichlorosilyl compounds, Tetrahedron, 2007,63, 3122-3132.
  • [13] Shimoda Y., Tando T., Kotani S., Sugiura M., Nakajima M.,Enantioselective aldol reaction of silyl ketene acetals promotedby a Lewis base-activated Lewis acid catalyst, Tetrahedron:Asymmetry, 2009, 20, 1369-1370.
  • [14] Kotani S., Aoki S., Sugiura M., Ogasawara, M., Nakajima M.,Phosphine Oxide-Catalyzed Enantioselective IntramolecularAldol Reaction via Regioselective Enolization of UnsymmetricalDiketones with Tetrachlorosilane, Org. Lett., 2014, 16,4802-4805.
  • [15] Genoni A., Benaglia M., Rossi S., Celentano G., EnantiomericallyPure Bithiophene Diphosphine Oxides as Catalysts forDirect Double Aldol Reactions, Chirality, 2013, 25, 643-647.
  • [16] Rossi S., Benaglia M., Genoni A., Benincori T., Celentano G.,Biheteroaromatic diphosphine oxides-catalyzed stereoselectivedirect aldol reactions, Tetrahedron, 2011, 67, 158-166.
  • [17] Kotani S., Sugiura M., Nakajima M., Enantioselective AldolReactions Catalyzed by Chiral Phosphine Oxides, Chem. Rec.2013, 13, 362-370.
  • [18] Aoki S., Kotani S., Sugiura M., Nakajima M., Trichlorosilyltriflate-mediated enantioselective directed cross-aldol reactionbetween ketones using a chiral phosphine oxide as an organocatalyst,Chem. Commun., 2012, 48, 5524-5526.
  • [19] Shimoda Y., Kotani S., Sugiura M., Nakajima M., EnantioselectiveDouble Aldol Reaction Catalyzed by Chiral PhosphineOxide, Chem Eur. J., 2011, 17, 7992-7995.
  • [20] Kotani S., Aoki S., Sugiura M., Nakajima M., Trichlorosilyltriflate for enantioselective direct-type aldol reactionwith chiral phosphine oxide, Tetrahedron Lett., 2011, 52,2834-2836.
  • [21] Kotani S., Shimoda Y., Sugiura M., Nakajima M., Novel enantioselectivedirect aldol-type reaction promoted by a chiralphosphine oxide as an organocatalyst, Tetrahedron Lett., 2009,50, 4602-4605.
  • [22] Shimoda, Y., Kubo T., Sugiura M., Kotani S., Nakajima M.,Stereoselective Synthesis of Multiple Stereocenters by Usinga Double Aldol Reaction, Angew. Chem. Int. Ed., 2013, 52,3461-3464.
  • [23] Zhang P., Han Z., Wang Z., Ding K., Spiro[4,4]-1,6-Nonadiene-Based Diphosphine Oxides in Lewis Base Catalyzed AsymmetricDouble-Aldol Reactions, Angew. Chem. Int. Ed., 2013, 52,11054-11058.
  • [24] Nakajima M., Kotani S., Sugiura M., Enantioselective DoubleAldol Reactions Involving the Sequential Activation of SiliconTetrachloride by Chiral Phosphine Oxides, Synlett, 2014, 25,631-640.
  • [25] Bonsignore M., Benaglia M., Cozzi F., Genoni A., Rossi S.,Raimondi L., Readily available (S) proline-derived organocatalystsfor the Lewis acid-mediated Lewis base-catalyzedstereoselective aldol reactions of activated thioesters,Tetrahedron, 2012, 68, 8251-8255.
  • [26] Rossi S., Benaglia M., Cozzi F., Genoni A., Benincori T., OrganocatalyticStereoselective Direct Aldol Reaction of TrifluoroethylThioesters, Adv. Synth. Catal., 2011, 353, 848-854.
  • [27] Osakama K., Sugiura M., Nakajima M., Kotani S., Enantioselectivereductive aldol reaction using tertiary amine as hydridedonor, Tetrahedron Lett., 2012, 53, 4199-4201.
  • [28] Sugiura M., Sato N., Sonoda Y., Kotani S., Nakajima M.,Diastereo- and Enantioselective Reductive Aldol Reaction withTrichlorosilane Using Chiral Lewis Bases as organocatalysts,Chem, Asian J., 2010, 5, 478-481.
  • [29] Kotani S., Ito M., Nozaki H., Sugiura M., Ogasawara M.,Nakajima M., Enantioselective Morita–Baylis–Hillman reactioncatalyzed by a chiral phosphine oxide, Tetrahedron Lett., 2013,54, 6430-6433.
  • [30] Denmark S.E., Beutner G.L., Lewis Base Catalysis in OrganicSynthesis, Angew. Chem. Int. Ed., 2008, 47, 1560-1638.
  • [31] Benincori T., Cesarotti E., Piccolo O., Sannicolò F.,2,2’,5,5’-Tetramethyl-4,4’-bis(diphenylphoshino)-3,3’-bithiophene: A New, Very Efficient, Easily Accessible, ChiralBiheteroaromatic Ligand for Homogeneous StereoselectiveCatalysis, J. Org. Chem., 2000, 65, 2043-2047.
  • [32] In this case, an inseparable mixture of mono- bis- andtriphosphoric chloride products were obtained.
  • [33] Mashima K., Kusano K.-h., Sato N., Matsumura Y.-i., NozakiK., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., AkutagawaS., Takaya H., Cationic BINAP-Ru(II) Halide Complexes:Highly Efficient Catalysts for Stereoselective AsymmetricHydrogenation of alpha- and beta-Functionalized Ketones, J.Org. Chem., 1994, 59, 3064-3076.
  • [34] Yields were not optimized.
  • [35] For full characterization and spectroscopic data see: Rossi S.,Chiral Lewis bases activation of trichlorosilyl derivatives, PhDThesis, Università degli Studi di Milano, Milano, Italy, 2010.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_asorg-2015-0002
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