PtII-Catalyzed Synthesis of 9-Oxabicyclo[3.3.1]nona-2,6-dienes from 2-Alkynyl-1-carbonylbenzenes and Allylsilanes by an Allylation/Annulation Cascade†
Sabyasachi Bhunia
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorKuo-Chang Wang
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorRai-Shung Liu Prof. Dr.
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorSabyasachi Bhunia
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorKuo-Chang Wang
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorRai-Shung Liu Prof. Dr.
Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082
Search for more papers by this authorWe thank the National Science Council, Taiwan for support of this work.
Graphical Abstract
Platinum is key: A new catalytic synthesis of 9-oxabicyclo[3.3.1]nona-2,6-dienes from readily available 2-alkynyl-1-carbonylbenzenes, allylsilanes, and water is reported (see scheme). This reaction sequence is proposed to proceed through a series of three reactions, including allylation of the carbonyl group, hydroalkoxylation of the alkyne, and a new ene-oxonium annulation.
Supporting Information
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References
- 1For recent reviews and leading references, see
- 1aH. J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145–151;
- 1bH. J. Knolker, J. Prakt. Chem. 1997, 339, 304;
- 1cR. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 1992, 57, 6094;
- 1dJ. S. Panek, M. Yang, J. Am. Chem. Soc. 1991, 113, 9868.
- 2Selected examples, see
- 2aJ. M. Tinsley, W. R. Roush, J. Am. Chem. Soc. 2005, 127, 10818;
- 2bS. R. Angle, N. A. El-Said, J. Am. Chem. Soc. 2002, 124, 3608.
- 3S. R. Angle, N. A. El-Said, J. Am. Chem. Soc. 1999, 121, 10211.
- 4For addition of allylsilanes or allylstannanes to carbonyl derivatives by using AgI, CuII, PtII, and AuI, see selected examples:
- 4aA. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723;
- 4bM. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem. 2003, 68, 5593;
- 4cA. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, H. Yamamoto, Angew. Chem. 1999, 111, 3916;
10.1002/(SICI)1521-3757(19991216)111:24<3916::AID-ANGE3916>3.0.CO;2-V Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3701;10.1002/(SICI)1521-3773(19991216)38:24<3701::AID-ANIE3701>3.0.CO;2-D CAS PubMed Web of Science® Google Scholar
- 4dJ. Kruger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837;
- 4eS. Obika, H. Kono, Y. Yasui, R. Yanada, Y. Takemoto, J. Org. Chem. 2007, 72, 4462.
- 5C.-C. Lin, T.-M. Deng, A. Odedra, R.-S. Liu, J. Am. Chem. Soc. 2007, 129, 3798.
- 6
- 6aB. Wünsch, M. Zott, G. Höfner, Arch. Pharm. 1992, 325, 733;
- 6bB. Wünsch, M. Zott, G. Höfner, Arch. Pharm. 1993, 326, 823;
- 6cC. Ketterer, S. Grimme, E. Weckert, B. Wünsch, Tetrahedron: Asymmetry 2006, 17, 3046.
- 7
- 7aC. Maurin, F. Bailly, P. Cortelle, Curr. Med. Chem. 2003, 10, 1795;
- 7bR. Dupont, L. Jeanson, J.-F. Mouscadet, P. Cotelle, Bioorg. Med. Chem. Lett. 2001, 11, 3175;
- 7cR. Dupont, P. Cotelle, Tetrahedron Lett. 1998, 39, 8457.
- 8In wet dichloroethane (25 °C, 12 h), AgOTf, PPh3AuSbF6, and [PPh3AuOTf] led to complete consumption of starting aldehyde 1 a, but only [PPh3AuOTf] gave desired oxatricyclic species 3 in a 25 % yield.
- 9For the PtCl2/CO catalysis, see
- 9aA. Fürstner, C. Aïssa, J. Am. Chem. Soc. 2006, 128, 6306;
- 9bA. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024;
- 9cB. P. Taduri, S. M. A. Sohel, H.-M. Cheng, G.-Y. Lin, R.-S. Liu, Chem. Commun. 2007, 2530–2532;
- 9dH.-K. Chang, S. Datta, A. Das, R.-S. Liu, Angew. Chem. 2007, 119, 4828; Angew. Chem. Int. Ed. 2007, 46, 4744.
- 10The x-ray crystallographic data for compound 3 c has been deposited at the Cambridge Crystallographic Data Center (CCDC-677837 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif), and 1H NOE spectra of key compounds are provided in the Supporting Information.
- 111,2-dihydronaphthalene 6 was formed from [4+2] cycloaddition of benzopyrinium C and 1-methylstyrene (see below); this olefin arose from decomposition of allylsilane with a Brønsted acid when water was present.[13] In a control experiment, we obtained compound 6 (86 % yield) from PtCl2/CO-catalyzed cyclization of 4 c with 1-methylstyrene in hot toluene. See the leading paper: N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628;
10.1002/ange.200351390 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3504.
- 12For the mechanism of formation of chrysene 7, see A. Das, H.-H. Liao R.-S. Liu, J. Org. Chem. 2007, 72, 9214.
- 13For similar observations, see
- 13aY.-G. Hsu, S. Datta, C.-M. Ting, R.-S. Liu, Org. Lett. 2008, 10, 521;
- 13bS. Porcel, V. Löpez-Carrilo, C. Garcia-Yebra, A. M. Echavarren, Angew. Chem. 2008, 120, 1909;
10.1002/ange.200704500 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1883.
- 14For formation of 1H-isochromenes from hydroalkoxylation of alkyne, see reference [5e] and selected examples:
- 14aX. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953;
- 14bN. Asao, T. Nogami, K. Takahashi, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 764;
- 14cN. Asao, C. S. Chan, K. Takahashi, Y. Yamamoto, Tetrahedron 2005, 61, 11322.
- 15The calculations were done with Gaussian-98 package at level B3LYP/6-31+G*; details are provided in the Supporting information.
- 16For metal-catalyzed addition of a tethered phenol or enol to an enol ether of 1H-isochromenes, see: A. Beeler, S. Su, C. A. Singleton, J. A. Proco, Jr., J. Am. Chem. Soc. 2007, 129, 1413.
- 17Ketones are generally inactive toward metal-catalyzed allylation reactions.[1] The high yields of oxatricyclic products 5 a–5 d may arise from addition of allylsilane to benzopyrilium species C,[11] rather than by the mechanism proposed in Scheme 2. We thank one reviewer for this valuable comment.
