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Volumn 13, Issue 17, 2007, Pages 4823-4832

Dual reactivity pattern of allenolates "on water": The chemical basis for efficient allenolate-driven organocatalytic systems

Author keywords

Acetylides; Allenolates; Cycloaddition; Organocatalysis; Water chemistry

Indexed keywords

ACETYLIDES; ALLENOLATES; ORGANOCATALYSIS; WATER CHEMISTRY;

EID: 34250327977     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700227     Document Type: Article
Times cited : (59)

References (82)
  • 1
    • 0036736355 scopus 로고    scopus 로고
    • For origins, status, and future challenges of this current topic see
    • For origins, status, and future challenges of this current topic see: P.T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694.
    • (2002) Acc. Chem. Res , vol.35 , pp. 686-694
    • Anastas, P.T.1    Kirchhoff, M.M.2
  • 2
    • 0012219553 scopus 로고    scopus 로고
    • Eds, J. Clark, D. Macquarrie, Blackwell, Oxford
    • a) Handbook of Green Chemistry and Technology (Eds.: J. Clark, D. Macquarrie), Blackwell, Oxford, 2002;
    • (2002) Handbook of Green Chemistry and Technology
  • 3
    • 33645549833 scopus 로고    scopus 로고
    • for a pharmaceutical perspective of this issue see
    • b) for a pharmaceutical perspective of this issue see: J. L. Tucker, Org. Process Res. Dev. 2006, 10, 315-319;
    • (2006) Org. Process Res. Dev , vol.10 , pp. 315-319
    • Tucker, J.L.1
  • 4
    • 0000096302 scopus 로고    scopus 로고
    • for contribution of chemistry to the sustainable development see
    • c) for contribution of chemistry to the sustainable development see: M. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem. 2002, 114, 402-425;
    • (2002) Angew. Chem , vol.114 , pp. 402-425
    • Eissen, M.1    Metzger, J.O.2    Schmidt, E.3    Schneidewind, U.4
  • 5
    • 0036470488 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 414-436.
    • (2002) Chem. Int. Ed , vol.41 , pp. 414-436
    • Angew1
  • 7
    • 0001069588 scopus 로고
    • for a full account of the hydrophobic effects on simple organic reactions in water see
    • b) for a full account of the hydrophobic effects on simple organic reactions in water see R. Breslow, Acc. Chem. Res. 1991, 24, 159-164.
    • (1991) Acc. Chem. Res , vol.24 , pp. 159-164
    • Breslow, R.1
  • 9
    • 34250363073 scopus 로고    scopus 로고
    • Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, UK, 1998;
    • a) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, UK, 1998;
  • 12
    • 24044470646 scopus 로고    scopus 로고
    • b) C.-J. Li, Chem. Rev. 2005, 105, 3095-3166;
    • (2005) Chem. Rev , vol.105 , pp. 3095-3166
    • Li, C.-J.1
  • 13
    • 0036703508 scopus 로고    scopus 로고
    • for excellent discussions on the acceleration of organic reactions through aqueous solvent effects see
    • c) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772; for excellent discussions on the acceleration of organic reactions through aqueous solvent effects see:
    • (2002) Chem. Rev , vol.102 , pp. 2751-2772
    • Lindström, U.M.1
  • 17
    • 20344388819 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3275-3279.
    • (2005) Chem. Int. Ed , vol.44 , pp. 3275-3279
    • Angew1
  • 20
    • 6044269452 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
    • (2004) Chem. Int. Ed , vol.43 , pp. 5138-5175
    • Angew1
  • 21
    • 34250360232 scopus 로고    scopus 로고
    • Special issue on asymmetric, Eds, K. N. Houk, B. List
    • c) Special issue on asymmetric Organocatalysis, Acc. Chem, Res. 2004, 37 (Eds.: K. N. Houk, B. List).
    • (2004) Acc. Chem, Res , vol.37
    • Organocatalysis1
  • 22
    • 33745500082 scopus 로고    scopus 로고
    • For selected examples of organocatalyzed direct aldol reactions in water see: a
    • For selected examples of organocatalyzed direct aldol reactions in water see: a) Z. Jiang, Z. Liang, X. Wu, Y. Lu, Chem. Commun. 2006, 2801-2803;
    • (2006) Chem. Commun , pp. 2801-2803
    • Jiang, Z.1    Liang, Z.2    Wu, X.3    Lu, Y.4
  • 25
    • 32044463187 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 958-961;
    • (2006) Chem. Int. Ed , vol.45 , pp. 958-961
    • Angew1
  • 35
    • 7444260726 scopus 로고    scopus 로고
    • For selected examples of organocatalyzed Mannich reactions in water see: a
    • For selected examples of organocatalyzed Mannich reactions in water see: a) Y.-S. Wu, J. Cai, Z.-Y. Hu, G.-X. Lin, Tetrahedron Lett. 2004, 45, 8949-8952;
    • (2004) Tetrahedron Lett , vol.45 , pp. 8949-8952
    • Wu, Y.-S.1    Cai, J.2    Hu, Z.-Y.3    Lin, G.-X.4
  • 37
    • 33646142092 scopus 로고    scopus 로고
    • For examples of aqueous organocatalyzed Michael additions see: a N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
    • For examples of aqueous organocatalyzed Michael additions see: a) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
  • 40
    • 28844441269 scopus 로고    scopus 로고
    • For selected examples of Baylis-Hillman reactions in water see: a
    • For selected examples of Baylis-Hillman reactions in water see: a) A. Porcelle, C. M. Williams, B. D. Schwartz, I. R. Gentle, Synlett 2005, 2923-2926;
    • (2005) Synlett , pp. 2923-2926
    • Porcelle, A.1    Williams, C.M.2    Schwartz, B.D.3    Gentle, I.R.4
  • 46
    • 25444465184 scopus 로고    scopus 로고
    • For selected examples of organocatalyzed Diels-Alder reactions in water see: a
    • For selected examples of organocatalyzed Diels-Alder reactions in water see: a) M. Lemay, W. W. Ogilvie, Org. Lett. 2005, 7, 4141-4144;
    • (2005) Org. Lett , vol.7 , pp. 4141-4144
    • Lemay, M.1    Ogilvie, W.W.2
  • 53
    • 0010338666 scopus 로고
    • For a review including the seminal work of Winterfeldt see
    • a) For a review including the seminal work of Winterfeldt see: E. Winterfeldt, Angew. Chem. 1967, 79, 389;
    • (1967) Angew. Chem , vol.79 , pp. 389
    • Winterfeldt, E.1
  • 54
    • 84981786018 scopus 로고
    • for recent reviews
    • Angew. Chem. Int. Ed. Engl. 1967, 6, 423-434; for recent reviews,
    • (1967) Angew. Chem. Int. Ed. Engl , vol.6 , pp. 423-434
  • 56
    • 22944485617 scopus 로고    scopus 로고
    • c) S. Ma, Chem. Rev. 2005, 105, 2829-2871;
    • (2005) Chem. Rev , vol.105 , pp. 2829-2871
    • Ma, S.1
  • 60
    • 0030878922 scopus 로고    scopus 로고
    • For phosphine-catalyzed a-additions to alkynoates, see
    • For phosphine-catalyzed a-additions to alkynoates, see: B. M. Trost, G. R Dake, J. Am. Chem. Soc. 1997, 119, 7595-7596.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 7595-7596
    • Trost, B.M.1    Dake, G.R.2
  • 61
    • 33748632920 scopus 로고    scopus 로고
    • For a theoretical study of the phosphine-catalyzed reactions of allenoates and aldehydes as well as acrylates and imines see: T. Duckling, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643-3646, and references therein
    • For a theoretical study of the phosphine-catalyzed reactions of allenoates and aldehydes as well as acrylates and imines see: T. Duckling, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643-3646, and references therein.
  • 62
    • 33847274696 scopus 로고    scopus 로고
    • We categorize them as ABB' 3CRs to highlight their bimolecular nature (A and B), the dual role played by component B along the reaction pathway (B and B') and their 3-component chemical outcomes. For full details see: D. Tejedor, F. García-Tellado, Chem. Soc. Rev. 2007, 36, 484-491.
    • We categorize them as ABB' 3CRs to highlight their bimolecular nature (A and B), the dual role played by component B along the reaction pathway (B and B') and their 3-component chemical outcomes. For full details see: D. Tejedor, F. García-Tellado, Chem. Soc. Rev. 2007, 36, 484-491.
  • 65
    • 0342514511 scopus 로고
    • for a more recent precedent, see
    • c) for a more recent precedent, see: C. Larpent, G. Meignan, H. Patin, Tetrahedron 1990, 46, 6381-6398.
    • (1990) Tetrahedron , vol.46 , pp. 6381-6398
    • Larpent, C.1    Meignan, G.2    Patin, H.3
  • 66
    • 33745503743 scopus 로고    scopus 로고
    • Lithium chloride is a salt which increases the hydrophobic effect, that is, it salts out nonpolar materials dissolved in water (kosmotropic effect). For an excellent discussion see: P. H von Fiel, T. Schleich, Acc. Chem. Res. 1969, 2, 257-265.
    • Lithium chloride is a salt which increases the hydrophobic effect, that is, it "salts out" nonpolar materials dissolved in water (kosmotropic effect). For an excellent discussion see: P. H von Fiel, T. Schleich, Acc. Chem. Res. 1969, 2, 257-265.
  • 67
    • 31544442671 scopus 로고    scopus 로고
    • The Raphael rearrangement of aromatic propargylic alcohols to the corresponding α,β-unsaturated ketones is favored under these reaction conditions see:, and references therein
    • The Raphael rearrangement of aromatic propargylic alcohols to the corresponding α,β-unsaturated ketones is favored under these reaction conditions see: J. P. Sonye, K. Koide, Org. Lett. 2006, 8, 199-202, and references therein.
    • (2006) Org. Lett , vol.8 , pp. 199-202
    • Sonye, J.P.1    Koide, K.2
  • 69
    • 34250340442 scopus 로고    scopus 로고
    • For examples of metal-catalyzed alkynylations of nitrones see: a R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem. 2002, 114, 3180-3182;
    • For examples of metal-catalyzed alkynylations of nitrones see: a) R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem. 2002, 114, 3180-3182;
  • 70
    • 0037119338 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3054-3056, and references therein;
    • Angew. Chem. Int. Ed. 2002, 41, 3054-3056, and references therein;
  • 73
    • 33845552306 scopus 로고
    • for selected recent examples of [3+2] cycloadditions of nitrones and alkynes see
    • b) J. P. Freeman, Chem. Rev. 1983, 83, 241-261; for selected recent examples of [3+2] cycloadditions of nitrones and alkynes see:
    • (1983) Chem. Rev , vol.83 , pp. 241-261
    • Freeman, J.P.1
  • 76
    • 0000521341 scopus 로고    scopus 로고
    • For the metal-catalyzed regioselective synthesis of these heterocycles from propargylic N-hydroxylamines see: P. Aschwanden, D. E. Frantz, E. M. Carreira, Org. Lett. 2000, 2, 2331-2333
    • For the metal-catalyzed regioselective synthesis of these heterocycles from propargylic N-hydroxylamines see: P. Aschwanden, D. E. Frantz, E. M. Carreira, Org. Lett. 2000, 2, 2331-2333.
  • 77
    • 0026567914 scopus 로고    scopus 로고
    • The 1,3-DCR of nitrones and conjugated alkynes usually affords mixtures of both regioisomers. For a discussion see: H. G. Aurich, M. Franzke, H. P. Kesselheim, M. Rohr, Tetrahedron 1992, 48, 669-682.
    • The 1,3-DCR of nitrones and conjugated alkynes usually affords mixtures of both regioisomers. For a discussion see: H. G. Aurich, M. Franzke, H. P. Kesselheim, M. Rohr, Tetrahedron 1992, 48, 669-682.
  • 79
    • 0034693123 scopus 로고    scopus 로고
    • low diastereoselectivity was also found in the 1,3-DCR of a chiral erythrulose-derived nitrone and ethyl propiolate in refluxing toluene: M. Carda, R. Portolés, J. Murga, S. Uriel, J. A. Marco, L. R. Domingo, R. J. Zaragoza, H. Röper, J. Org. Chem. 2000, 65, 7000-7009.
    • b) low diastereoselectivity was also found in the 1,3-DCR of a chiral erythrulose-derived nitrone and ethyl propiolate in refluxing toluene: M. Carda, R. Portolés, J. Murga, S. Uriel, J. A. Marco, L. R. Domingo, R. J. Zaragoza, H. Röper, J. Org. Chem. 2000, 65, 7000-7009.
  • 80
    • 34250305875 scopus 로고    scopus 로고
    • At this stage of the work, we have not a clear answer to explain this selectivity profile. We are working on this issue in our group with more examples of carbohydrate-containing nitrones to see the possible generality of this effect. The results of this study will be published at due time elsewhere
    • At this stage of the work, we have not a clear answer to explain this selectivity profile. We are working on this issue in our group with more examples of carbohydrate-containing nitrones to see the possible generality of this effect. The results of this study will be published at due time elsewhere.
  • 81
    • 34250342148 scopus 로고    scopus 로고
    • [17] a poor dipolarophile and an excellent precursor of phosphorous-containing allylic anions IV (see Scheme 2).
    • [17] a poor dipolarophile and an excellent precursor of phosphorous-containing allylic anions IV (see Scheme 2).
  • 82
    • 22244463229 scopus 로고    scopus 로고
    • The electronic difference between both heteroatoms usually determines the chemical reactivity of the allenolates and as a consequence, the chemical outcome of the catalytic process. For a recent example see: Y, Ling, M. Shi, Org. Lett. 2005, 7, 3057-3060. For other examples see reference [17
    • The electronic difference between both heteroatoms usually determines the chemical reactivity of the allenolates and as a consequence, the chemical outcome of the catalytic process. For a recent example see: Y. -Ling, M. Shi, Org. Lett. 2005, 7, 3057-3060. For other examples see reference [17].


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