Highly Efficient Catalytic Formation of (Z)-1,4-But-2-ene Diols Using Water as a Nucleophile
Dr. Wusheng Guo
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
These authors contributed equally to this work.
Search for more papers by this authorLuis Martínez-Rodríguez
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
These authors contributed equally to this work.
Search for more papers by this authorDr. Eddy Martin
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorEduardo C. Escudero-Adán
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Arjan W. Kleij
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona, Spain
Search for more papers by this authorDr. Wusheng Guo
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
These authors contributed equally to this work.
Search for more papers by this authorLuis Martínez-Rodríguez
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
These authors contributed equally to this work.
Search for more papers by this authorDr. Eddy Martin
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorEduardo C. Escudero-Adán
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Arjan W. Kleij
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona, Spain
Search for more papers by this authorAbstract
The first general catalytic and highly stereoselective formation of (Z)-1,4-but-2-ene diols is described from readily available and modular vinyl-substituted cyclic carbonate precursors using water as a nucleophilic reagent. These 1,4-diol scaffolds can be generally prepared in high yields and with ample scope in reaction partners using a simple synthetic method that does not require the presence of any additive or any special precaution unlike the stoichiometric approaches reported to date. Control experiments support the mechanistic view that hyperconjugation within the catalytic intermediate after decarboxylation plays an imperative role to control the stereoselective outcome of these reactions.
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References
- 1
- 1aE. Bode, M. Wolberg, M. Müller, Synthesis 2006, 557–558;
- 1bH. C. Kolb, M. S. VanNieuwenhuize, K. B. Sharpless, Chem. Rev. 1994, 94, 2483–2547;
- 1cH. R. Kricheldorf, J. Macromol. Sci., C: Polym. Rev. 1997, 37, 599–631;
- 1dC. J. R. Bataille, T. J. Donohoe, Chem. Soc. Rev. 2011, 40, 114–128; Use of diols for polyurethane preparations:
- 1eH.-W. Engels, H.-G. Pirkl, R. Albers, R. W. Albach, J. Krause, A. Hoffmann, H. Casselmann, J. Dormish, Angew. Chem. Int. Ed. 2013, 52, 9422–9441; Angew. Chem. 2013, 125, 9596–9616; In hydrolytic kinetic resolution:
- 1fE. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421–431.
- 2M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936–938.
- 3
- 3aE. N. Jacobsen, I. Marko, W. S. Mungall, G. Schroeder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968–1970;
- 3bH. C. Kolb, P. G. Anderson, K. B. Sharpless, J. Am. Chem. Soc. 1994, 116, 1278–1291; For a recent diastereoselective approach towards syn-diols from cyclic carbonate precursors see:
- 3cV. Laserna, G. Fiorani, C. J. Whiteoak, E. Martin, E. Escudero-Adán, A. W. Kleij, Angew. Chem. Int. Ed. 2014, 53, 10416–10419; Angew. Chem. 2014, 126, 10584–10587.
- 4D. Craig, S. J. Gore, M. I. Lansdell, S. E. Lewis, A. V. W. Mayweg, A. J. P. White, Chem. Commun. 2010, 46, 4991–4993.
- 5K. Klimovica, L. Grigorjeva, A. Maleckis, J. Popelis, A. Jirgensons, Synlett 2011, 2849–2851.
- 6X. Xie, S. S. Stahl, J. Am. Chem. Soc. 2015, 137, 3767–3770.
- 7M. J. Koh, R. K. M. Khan, S. Torker, M. Yu, M. S. Mikus, A. H. Hoveyda, Nature 2015, 517, 181–186.
- 8The only known catalytic method towards (Z)-but-2-ene diols (only one example) is based on the Pd-mediated hydroarylation of alkynes using arylboronic acids at 80 °C in 1,4-dioxane; see:
- 8aC. H. Oh, H. H. Jung, K. S. Kim, N. Kim, Angew. Chem. Int. Ed. 2003, 42, 805–808; Angew. Chem. 2003, 115, 829–832;
- 8bA. K. Gupta, K. S. Kim, C. H. Oh, Synlett 2005, 457–460.
- 9
- 9aA. Khan, L. Yang, J. Xu, L. Y. Jin, Y. J. Zhang, Angew. Chem. Int. Ed. 2014, 53, 11257–11260; Angew. Chem. 2014, 126, 11439–11442;
- 9bA. Khan, R. Zheng, Y. Kan, J. Ye, J. Xing, Y. J. Zhang, Angew. Chem. Int. Ed. 2014, 53, 6439–6442; Angew. Chem. 2014, 126, 6557–6560;
- 9cK. Ohmatsu, N. Imagawa, T. Ooi, Nat. Chem. 2014, 6, 47–51; For other recent relevant examples see:
- 9dA. Khan, J. Xing, J. Zhao, Y. Kan, W. Zhang, Y. J. Zhang, Chem. Eur. J. 2015, 21, 120–124;
- 9eL. Yang, A. Khan, R. Zheng, L. Y. Jin, Y. J. Zhang, Org. Lett. 2015, 17, 6230–6233;
- 9fA. Khan, Y. J. Zhang, Synlett 2015, 26, 853–860.
- 10
- 10aG. Dong, P. Teo, Z. K. Wickens, R. H. Grubbs, Science 2011, 333, 1609–1612;
- 10bQ.-K. Kang, L. Wang, Q.-J. Liu, J.-F. Li, Y. Tang, J. Am. Chem. Soc. 2015, 137, 14594–14597; recently Sanford and Lee reported the in situ nucleophilic substitution of an alkyl chloride by water in the site-selective C−H oxidation of amines at 150 °C; see:
- 10cM. Lee, M. S. Sanford, J. Am. Chem. Soc. 2015, 137, 12796–12799; for related allylic hydroxylation, see:
- 10dB. J. Lüssem, H. J. Gais, J. Am. Chem. Soc. 2003, 125, 6066–6067;
- 10eN. Kanbayashi, K. Onitsuka, Angew. Chem. Int. Ed. 2011, 50, 5197–5199; Angew. Chem. 2011, 123, 5303–5305;
- 10fM. Gärtner, S. Mader, K. Seehafer, G. Helmchen, J. Am. Chem. Soc. 2011, 133, 2072–2075.
- 11The White catalyst is a bis(sulfoxide) ligated Pd(OAc)2 precursor that has shown high potential in various allylic conversions; see for example:
- 11aC. C. Pattillo, I. I. Strambeanu, P. Calleja, N. A. Vermeulen, T. Mizuno, M. C. White, J. Am. Chem. Soc. 2016, 138, 1265–1272;
- 11bE. M. Stang, M. C. White, Nat. Chem. 2009, 1, 547–551.
- 12Note that if larger excess of H2O was used, the reaction was completely shut down.
- 13CCDC 1465246 contains the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.
- 14Simple hydrolysis of cyclic carbonates towards 1,2-diols has been well-documented; see for example:
- 14aP. Le Gendre, T. Braun, C. Bruneau, P. H. Dixneuf, J. Org. Chem. 1996, 61, 8453–8455;
- 14bC. Beattie, M. North, P. Villuendas, C. Young, J. Org. Chem. 2013, 78, 419–426;
- 14cS. Sarel, I. Levin, L. A. Pohoryles, J. Chem. Soc. 1960, 3079–3082; see also Ref. [3c].
- 15
- 15aM. Sekine, T, Hata, J. Am. Chem. Soc. 1983, 105, 2044–2049;
- 15bJ. J. Bozell, D. Miller, B. R. Hames, C. Loveless, J. Org. Chem. 2001, 66, 3084–3089.
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