N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones
Lihui Sun
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorTong Wang
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, ChinaSearch for more papers by this authorLihui Sun
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorTong Wang
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, ChinaSearch for more papers by this authorAbstract
In contrast with the reported phosphine- and DABCO-catalyzed [3+2] and [2+2] annulation of allenoates with trifluoromethylketone, the [2+2+2] annulation of allenoates and two molecules of trifluoromethylketone was found under the condition of N-heterocyclic carbene catalysis.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
| Filename | Description |
|---|---|
| cjoc_201100383_sm_suppl.pdf744.7 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1For rewiews, see:
- 1a Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A.. Chem. Rev., 2000, 100, 3067.
- 1b Lu, X.; Zhang, C.; Xu, Z.. Acc. Chem. Res., 2001, 34, 535.
- 1c Methot, J. L.; Roush, W. R.. Adv. Synth. Catal., 2004, 346, 1035.
- 1d Lu, X.; Du, Y.; Lu, C.. Pure Appl. Chem., 2005, 77, 1985.
- 1e Ma, S. M.. Aldrichimica Acta., 2007, 40, 91.
- 1f Ye, L.-W.; Zhou, J.; Tang, Y.. Chem. Soc. Rev., 2008, 37, 1140.
- 1g Cowen, B. J.; Miller, S. J.. Chem. Soc. Rev., 2009, 38, 3102.
- 2 Zhang, C.; Lu, X.. J. Org. Chem., 1995, 60, 2906.
- 3 Lu, Z.; Lu, X.. Tetrahedron Lett., 1997, 38, 3461.
- 4a Zhu, X.-F.; Lan, J.; Kwon, O.. J. Am. Chem. Soc., 2003, 125, 4716.
- 4b Zhao, G.-L.; Shi, M.. Org. Biomol. Chem., 2005, 3, 3686.
- 4c Tran, Y. S.; Kwon, O.. J. Am. Chem. Soc., 2007, 129, 12632.
- 4d Wurz, R. P.; Fu, G. C.. J. Am. Chem. Soc., 2005, 127, 12234.
- 5a Du, Y.; Lu, X.; Yu, Y.. J. Org. Chem., 2002, 67, 8901.
- 5b Lu, X.; Lu, Z.; Zhang, X.. Tetrahedron, 2006, 62, 457.
- 5c Lu, Z.; Zheng, S.; Zhang, X.; Lu, X.. Org. Lett., 2008, 10, 3267.
- 5d Wallace, D. J.; Sidda, R. L.; Reamer, R. A.. J. Org. Chem., 2007, 72, 1051.
- 5e Sampath, M.; Loh, T.-P.. Chem. Commun., 2009, 1568.
- 5f Henry, C. E.; Kwon, O.. Org. Lett., 2007, 9, 3069.
- 5g Shu, L.-H.; Sun, W.-Q.; Zhang, D.-W.; Wu, S.-H.; Wu, H.-M.; Xu, J.-F.; Lao, X.-F.. Chem. Commun., 1997, 79.
- 5h O'Donovan, B. F.; Hitchcock, P. B.; Meidine, M. F.; Kroto, H. W.; Taylor, R.; Walton, D. R. M.. Chem. Commun., 1997, 81.
- 5i Dudding, T.; Kwon, O.; Mercier, E.. Org. Lett., 2006, 8, 3643.
- 5j Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X.. J. Am. Chem. Soc., 2007, 129, 3470.
- 5k Ruano, J. L. G.; Nunez, Jr.A.; Rosario Martin, M.; Fraile, A.. J. Org. Chem., 2008, 73, 9366.
- 5l Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S.. Org. Lett., 2000, 2, 2023.
- 5m Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H.. J. Org. Chem., 2005, 70, 6369.
- 5n For the asymmetric Lu reaction, see: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, X.; Cao, P.; Zhang, X.. J. Am. Chem. Soc., 1997, 119, 3836.
- 5o Wilson, J.; Fu, G. C.. Angew. Chem. Int. Ed., 2006, 45, 1426.
- 5p Cowen, B. J.; Miller, S. J.. J. Am. Chem. Soc., 2007, 129, 10988.
- 5q Voituriez, A.; Panossian, A.; Fleury-Bregeot, N.; Retailleau, P.; Marinetti, A.. J. Am. Chem. Soc., 2008, 130, 14030.
- 5r Xiao, H.; Chai, Z.; Zheng, C.-W.; Yang, Y-Q.; Liu, W.; Zhang, J.-K.; Zhao, G.. Angew. Chem., Int. Ed., 2010, 49, 4467.
- 6a Wang, J.-C.; Krische, M. J.. Angew. Chem., Int. Ed., 2003, 42, 5855.
- 6b Du, Y.; Lu, X.. J. Org. Chem., 2003, 68, 6463.
- 6c Jones, R. A.; Krische, M. J.. Org. Lett., 2009, 11, 1849.
- 7 Tsubio, S.; Kuroda, H.; Takatsuku, S.; Fukawa, T.; Sakai, T.; Utak, M.. J. Org. Chem., 1993, 58, 5952.
- 8a Evans, C. A.; Miller, S. J.. J. Am. Chem. Soc., 2003, 125, 12394.
- 8b Zhao, G.-L.; Huang, J.-W.; Shi, M.. Org. Lett., 2003, 5, 4737.
- 8c Shi, Y.-L.; Shi, M.. Org. Lett., 2005, 7, 3057.
- 8d Dai, L.-Z.; Shi, Y.-L.; Zhao, G.-L.; Shi, M.. Chem. Eur. J., 2007, 13, 3701.
- 8e Crown, B. J.; Saunders, L. B.; Miller, S. J.. J. Am. Chem. Soc., 2009, 131, 6105.
- 8f Guan, X.-Y.; Wei, Y.; Shi, M.. J. Org. Chem., 2009, 74, 6343.
- 8g Denis, J.-B.; Masson, G.; Retailleau, P.; Zhu, J.. Angew. Chem., Int. Ed., 2011, 50, 5356.
- 9a Igau, A.; Grützmaxher, H.; Baceiredo, A.; Bertrand, G.. J. Am. Chem. Soc., 1988, 110, 6463.
- 9b Arduengo, A. J., III; Harlow, R. L.; Kline, M.. J. Am. Chem. Soc., 1991, 113, 361.
- 10For reviews, see:
- 10a Enders, D.; Balensiefer, T.. Acc. Chem. Res., 2004, 37, 534.
- 10b Enders, D.; Niemeier, O.; Henseler, A.. Chem. Rev., 2007, 107, 5606.
- 10c Rovis, T.. Chem. Lett., 2008, 37, 2.
- 10d Arduengo, III, A. J.; Iconaru, L. I.. Dalton Trans., 2009, 35, 6903.
- 10e Moore, J. L.; Rovis, T.. Top. Curr. Chem., 2010, 291, 77.
- 10f Sun, X.-Y.; Wu, J.. Chin. J. Org. Chem., 2006, 26, 745.
- 11For examples, see:
- 11a Breslow, R.. J. Am. Chem. Soc., 1958, 80, 3719.
- 11b Burstein, C.; Glorius, F.. Angew. Chem., Int. Ed., 2004, 43, 6205.
- 11c Chow, K. Y. K.; Bode, J. W.. J. Am. Chem. Soc., 2004, 126, 8126.
- 11d Reynolds, N. T.; Rovis, T.. J. Am. Chem. Soc., 2005, 127, 16406.
- 11e Enders, D.; Niemeier, O.; Balensiefer, T.. Angew. Chem., Int. Ed., 2006, 45, 1463.
- 11f Wu, J.; Sun, X.; Ye, S.; Sun, W.. Tetrahedron Lett., 2006, 47, 4813.
- 11g Liu, Y.-K.; Li, R.; Yue, L.; Li, B.-J.; Chen, Y.-C.; Wu, Y.; Ding, L.-S.. Org. Lett., 2006, 8, 1521.
- 11h Li, G.-Q.; Li, Y.; Dai, L.-X.; You, S.-L.. Org. Lett., 2007, 9, 3519.
- 11i Chan, A.; Scheidt, K. A.. J. Am. Chem. Soc., 2007, 129, 5334.
- 11j Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S.. Org. Lett., 2008, 10, 277.
- 11k Li, Y.; Feng, Z.; You, S.-L.. Chem. Commun., 2008, 2263.
- 11l Lin, L.; Li, Y.; Du, W.; Deng, W.-P.. Tetrahedron Lett., 2010, 51, 3571.
- 11m Awasthi, C.; Yadav, L. D. S.. Synlett, 2010, 1783.
- 11n Huang, X.-L.; Ye, S.. Chinese Sci. Bull., 2010, 55, 1753.
- 11o
Wang, T.;
Ye, S..
Sci. Sin. Chim.,
2011,
41,
1306.
10.1360/032011-179 Google Scholar
- 12 Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C.. J. Am. Chem. Soc., 2006, 128, 1472.
- 13 He, L.; Jian, T.-Y.; Ye, S.. J. Org. Chem., 2007, 72, 7466.
- 14a Wang, T.; Ye, S.. Org. Lett., 2010, 12, 4168.
- 14b Wang, T.; Ye, S.. Org. Biomol. Chem., 2011, 9, 5260.
- 14c Wang, T.; Ye, S.. Tetrahedron Lett., 2011, 52, 5488.
- 15For selected publications on fluorine chemistry, see:
- 15a Ma, J. A.; Cahard, D.. Chem. Rev., 2004, 104, 6119.
- 15b Uneyama, K.; Katagiri, T.; Amii, H.. Acc. Chem. Res., 2008, 41, 817.
- 15c
Fernández, R.;
Martín-Zamora, E.;
Pareja, C.;
Vázquez, J.;
Díez, E.;
Monge, A.;
Lassaletta, J. M..
Angew. Chem., Int. Ed.,
1998,
37,
3428.
10.1002/(SICI)1521-3773(19981231)37:24<3428::AID-ANIE3428>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 15d
Bøgevig, A.;
Gothelf, K. V.;
Jørgensen, K. A..
Chem. Eur. J.,
2002,
8,
5652.
10.1002/1521-3765(20021216)8:24<5652::AID-CHEM5652>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- 15e Zhao, J.-L.; Liu, L.; Gu, C.-L.; Wang, D.; Chen, Y.-J.. Tetrahedron Lett., 2008, 49, 1476.
- 15f Shi, M.; Liu, X.-G.; Guo, Y.-W.; Zhang, W.. Tetrahedron, 2007, 63, 12731.
- 16 The crystals were prepared by slow evaporation of the solvent of a solution of, trans- and, cis-4a in petroleum/ethyl acetate (20:1) at room temperature. CCDC 855010 (cis-4a), 855011 (trans-4a) contain the crystallographic data in this paper.
