메뉴 건너뛰기




Volumn 34, Issue 6, 2013, Pages 596-605

Chiral non-racemic sulfoxides by asymmetric alkylation of alkanesulfenates in the presence of a chiral ammonium phase-transfer catalyst derived from Cinchona alkaloid

Author keywords

Cinchona alkaloid; organocatalysis; phase transfer; sulfenate salt; sulfoxide

Indexed keywords

ALKALOIDS; CATALYSTS; METABOLITES;

EID: 84889589531     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415993.2013.795226     Document Type: Article
Times cited : (21)

References (29)
  • 2
    • 77955206605 scopus 로고    scopus 로고
    • Enantioselective synthesis of sulfoxides 2000- 2009
    • Wojaczyñska E, Wojaczỳnski J. Enantioselective synthesis of sulfoxides 2000 - 2009. Chem Rev. 2010;110:4303-4356.
    • (2010) Chem Rev. , vol.110 , pp. 4303-4356
    • Wojaczyñska, E.1    Wojaczỳnski, J.2
  • 4
    • 36849024926 scopus 로고    scopus 로고
    • Chiral sulfur ligands for asymmetric catalysis
    • DOI 10.1021/cr068440h
    • Mellah M, Voituriez A, Schulz E. Chiral sulfur ligands for asymmetric catalysis. Chem Rev. 2007;107:5133-5209. (Pubitemid 350225872)
    • (2007) Chemical Reviews , vol.107 , Issue.11 , pp. 5133-5209
    • Mellah, M.1    Voituriez, A.2    Schulz, E.3
  • 5
    • 0141508049 scopus 로고    scopus 로고
    • Recent developments in the synthesis and utilization of chiral sulfoxides
    • Fernández I, Khiar N. Recent developments in the synthesis and utilization of chiral sulfoxides. Chem Rev. 2003;103:3651-3706.
    • (2003) Chem Rev. , vol.103 , pp. 3651-3706
    • Fernández, I.1    Khiar, N.2
  • 7
    • 77951115195 scopus 로고    scopus 로고
    • Penilumamide a novel lumazine peptide isolated from the marine-derived fungus penicillium sp CNL-338
    • Meyer SW, Mordhorst TF, Lee C, Jensen PR, FenicalW, Köck M. Penilumamide, a novel lumazine peptide isolated from the marine-derived fungus, Penicillium sp. CNL-338. Org Biomol Chem 2010;8:2158-2163.
    • (2010) Org Biomol Chem , vol.8 , pp. 2158-2163
    • Meyer, S.W.1    Mordhorst, T.F.2    Lee, C.3    Jensen, P.R.4    Fenical, W.5    Köck, M.6
  • 8
    • 85195227955 scopus 로고    scopus 로고
    • Esomeprazolewas the third largest selling drug in 2011 ($6.156 billion U.S.): Top 200 Products of 2011 by Total Dollars. 7851 [cited 2012 July 10] Available from
    • Esomeprazolewas the third largest selling drug in 2011 ($6.156 billion U.S.): Top 200 Products of 2011 by Total Dollars. Pharmacy Times. 2012;78:51 [cited 2012 July 10]. Available from: Http://www.pharmacytimes.com/- media/-pdf/Top-200-Drugs-2011-Total-Dollars.pdf
    • (2012) Pharmacy Times.
  • 10
    • 84859956060 scopus 로고    scopus 로고
    • Chiral phosphoric acid-catalyzed asymmetric oxidation of aryl alkyl sulfides and aldehyde-derived 1, 3-dithianes: Using aqueous hydrogen peroxide as the terminal oxidant
    • Liu ZM, Zhao H, LiMQ, LanYB, Yao QB, Tao JC, WangXW. Chiral phosphoric acid-catalyzed asymmetric oxidation of aryl alkyl sulfides and aldehyde-derived 1, 3-dithianes: Using aqueous hydrogen peroxide as the terminal oxidant. Adv Synth Catal. 2012;354:1012-1022.
    • (2012) Adv Synth Catal. , vol.354 , pp. 1012-1022
    • Liu, Z.M.1    Zhao, H.2    Li, M.Q.3    Lan, Y.B.4    Yao, Q.B.5    Tao, J.C.6    Wang, X.W.7
  • 11
    • 84863521201 scopus 로고    scopus 로고
    • Activation of H2O2 by chiral confined Brønsted acids: A highly enantioselective catalytic sulfoxidation
    • Liao S, Č orić I, Wang Q, List B. Activation of H2O2 by chiral confined Brønsted acids: A highly enantioselective catalytic sulfoxidation. J Am Chem Soc. 2012;134:10765-10768.
    • (2012) J Am Chem Soc. , vol.134 , pp. 10765-10768
    • Liao, S.1    Čorić, I.2    Wang, Q.3    List, B.4
  • 12
    • 17044413284 scopus 로고    scopus 로고
    • Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides
    • Caupène C, Boudou C, Perrio S, Metzner P. Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides. J Org Chem. 2005;70:2812-2815.
    • (2005) J Org Chem. , vol.70 , pp. 2812-2815
    • Caupène, C.1    Boudou, C.2    Perrio, S.3    Metzner, P.4
  • 13
    • 0041702197 scopus 로고    scopus 로고
    • Novel approach to the synthesis of enantioenriched sulfoxides Highly diastereoselective alkylation of sulfenate anions with 1, 4-Asymmetric induction
    • Sandrinelli F, Perrio S, Averbuch-Pouchot MT. Novel approach to the synthesis of enantioenriched sulfoxides. Highly diastereoselective alkylation of sulfenate anions with 1, 4-Asymmetric induction. Org Lett. 2002;4:3619-3622.
    • (2002) Org Lett. , vol.4 , pp. 3619-3622
    • Sandrinelli, F.1    Perrio, S.2    Averbuch-Pouchot, M.T.3
  • 14
    • 34249017980 scopus 로고    scopus 로고
    • 2-(trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions
    • DOI 10.1055/s-2007-966017
    • Foucoin F, Caupène C, Lohier JF, Sopková-de Oliveira Santos J, Perrio S, Metzner P. 2-(Trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions. Synthesis. 2007;1315-1324. (Pubitemid 46797607)
    • (2007) Synthesis , Issue.9 , pp. 1315-1324
    • Foucoin, F.1    Caupene, C.2    Lohier, J.-F.3    Santos, J.S.D.O.4    Perrio, S.5    Metzner, P.6
  • 15
    • 79958780921 scopus 로고    scopus 로고
    • Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a Cinchona-derived phase-Transfer reagent
    • Gelat F, Jayashankaran J, Lohier JF, Gaumont AC, Perrio S. Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a Cinchona-derived phase-Transfer reagent.Org Lett. 2011;13:3170-3173.
    • (2011) Org Lett. , vol.13 , pp. 3170-3173
    • Gelat, F.1    Jayashankaran, J.2    Lohier, J.F.3    Gaumont, A.C.4    Perrio, S.5
  • 16
    • 3142684447 scopus 로고    scopus 로고
    • Generation structure and reactions of sulfenic acid anions
    • O'Donnell, JS, SchwanAL. Generation, structure and reactions of sulfenic acid anions. J Sulfur Chem. 2004;25:183-211.
    • (2004) J Sulfur Chem. , vol.25 , pp. 183-211
    • O'Donnell, J.S.1    Schwan, A.L.2
  • 19
    • 84876234339 scopus 로고    scopus 로고
    • Recent developments in asymmetric phasetransfer reactions
    • Shirakawan S, Maruoka K. Recent developments in asymmetric phasetransfer reactions. Angew Chem Int Ed. 2013;52:4312-4348.
    • (2013) Angew Chem Int E.d. , vol.52 , pp. 4312-4348
    • Shirakawan, S.1    Maruoka, K.2
  • 20
    • 70450190820 scopus 로고    scopus 로고
    • Cinchona-based phase-Transfer catalysts for asymmetric synthesis
    • Jew SS, Park HG. Cinchona-based phase-Transfer catalysts for asymmetric synthesis. Chem Commun. 2009;45:7090-7103.
    • (2009) Chem Commun. , vol.45 , pp. 7090-7103
    • Jew, S.S.1    Park, H.G.2
  • 21
    • 84862985015 scopus 로고    scopus 로고
    • Kinetic resolution of α-bromophenylacetamides using quinine or Cinchona alkaloid salts
    • Marzorati L, Fejfar JL, Tormena CF, Di Vitta C. Kinetic resolution of α-bromophenylacetamides using quinine or Cinchona alkaloid salts. Tetrahedron: Asymmetry. 2012;23:748-753.
    • (2012) Tetrahedron: Asymmetry. , vol.23 , pp. 748-753
    • Marzorati, L.1    Fejfar, J.L.2    Tormena, C.F.3    Di Vitta, C.4
  • 22
    • 0346970844 scopus 로고    scopus 로고
    • Fluorinated Alcohols: A New Medium for Selective and Clean Reaction
    • Bégué JP, Bonnet-Delpon D, Crousse B. Fluorinated alcohols: A newmedium for selective and clean reaction. Synlett. 2004;18-29. (Pubitemid 38067788)
    • (2004) Synlett , Issue.1 , pp. 18-29
    • Begue, J.-P.1    Bonnet-Delpon, D.2    Crousse, B.3
  • 23
    • 84873971783 scopus 로고    scopus 로고
    • Sulfenate substitution as a complement and alternative to sulfoxidation in the diastereoselective preparation of chiral β-substituted β-Amino sulfoxides
    • Söderman SC, Schwan AL. Sulfenate substitution as a complement and alternative to sulfoxidation in the diastereoselective preparation of chiral β-substituted β-Amino sulfoxides. J Org Chem. 2013;78:1638-1649.
    • (2013) J Org Chem. , vol.78 , pp. 1638-1649
    • Söderman, S.C.1    Schwan, A.L.2
  • 24
    • 77949812795 scopus 로고    scopus 로고
    • Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
    • Singh SP, O'Donnell JS, Schwan AL. Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions. Org Biomol Chem. 2010;8:1712-1717.
    • (2010) Org Biomol Chem. , vol.8 , pp. 1712-1717
    • Singh, S.P.1    O'Donnell, J.S.2    Schwan, A.L.3
  • 25
    • 71149090332 scopus 로고    scopus 로고
    • Mild and efficient access to lithium alkanesulfinates based on oxaziridine-promoted oxidation of thiolates
    • Caupène C, Martin C, Lemarié M, Perrio S, Metzner P. Mild and efficient access to lithium alkanesulfinates based on oxaziridine-promoted oxidation of thiolates. J Sulfur Chem. 2009;30:338-345.
    • (2009) J Sulfur Chem. , vol.30 , pp. 338-345
    • Caupène, C.1    Martin, C.2    Lemarié, M.3    Perrio, S.4    Metzner, P.5
  • 26
    • 0034685219 scopus 로고    scopus 로고
    • Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiols
    • DOI 10.1016/S0040-4039(99)02269-8, PII S0040403999022698
    • Palomo C, Oiarbide M, López R, Gómez-Bengoa E. Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiols. Tetrahedron Lett. 2000;41:1283-1286. (Pubitemid 30117353)
    • (2000) Tetrahedron Letters , vol.41 , Issue.8 , pp. 1283-1286
    • Palomo, C.1    Oiarbide, M.2    Lopez, R.3    Gomez-Bengoa, E.4
  • 27
    • 0035902407 scopus 로고    scopus 로고
    • Enantioselective solution- and solid-phase synthesis of glutamic acid derivatives via Michael addition reactions
    • DOI 10.1016/S0957-4166(01)00116-1, PII S0957416601001161
    • O'Donnell MJ, Delgado F, Domínguez E, de Blas J, Scott WL. Enantioselective solution- And solid-phase synthesis of glutamic acid derivatives via Michael addition reactions. Tetrahedron: Asymmetry. 2001;12:821-828. (Pubitemid 32522734)
    • (2001) Tetrahedron Asymmetry , vol.12 , Issue.6 , pp. 821-828
    • O'Donnell, M.J.1    Delgado, F.2    Dominguez, E.3    De Blas, J.4    Scott, W.L.5
  • 29
    • 34547406870 scopus 로고    scopus 로고
    • Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water
    • DOI 10.1021/ja071916+
    • Egami H, Katsuki T. Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water. J Am Chem Soc. 2007;129:8940-8941. (Pubitemid 47171824)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.29 , pp. 8940-8941
    • Egami, H.1    Katsuki, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.