Asymmetric Synthesis of a Fused Tricyclic Hydronaphthofuran Scaffold by Desymmetric [2+2+2] Cycloaddition
Qi Teng
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorWenxiu Mao
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorDong Chen
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorZhen Wang
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorProf. Dr. Chen-Ho Tung
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenghu Xu
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorQi Teng
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorWenxiu Mao
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorDong Chen
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorZhen Wang
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorProf. Dr. Chen-Ho Tung
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenghu Xu
Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorDedicated to Professor Li-Xin Dai on the occasion of his 95th birthday
Graphical Abstract
A rhodium(I)-BINAP-catalyzed [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo-, regio-, diastereo-, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions.
Abstract
A rhodium(I)-BINAP-catalyzed highly enantioselective [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo-, regio-, diastereo-, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
anie201911071-sup-0001-misc_information.pdf62.3 MB | Supplementary |
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
- 1
- 1aJ. Jauch, Angew. Chem. Int. Ed. 2008, 47, 34; Angew. Chem. 2008, 120, 34;
- 1bJ. Germain, P. Deslongchamps, J. Org. Chem. 2002, 67, 5269;
- 1cS. Hanessian, N. Boyer, G. J. Reddy, B. Deschênes-Simard, Org. Lett. 2009, 11, 4640.
- 2
- 2aH. Ye, G. Deng, J. Liu, F. G. Qiu, Org. Lett. 2009, 11, 5442;
- 2bD.-S. Hsu, C.-C. Liao, Org. Lett. 2003, 5, 4741;
- 2cK. C. Nicolaou, Y. H. Lim, J. Becker, Angew. Chem. Int. Ed. 2009, 48, 3444; Angew. Chem. 2009, 121, 3496;
- 2dX. Liu, C.-S. Lee, Org. Lett. 2012, 14, 2886.
- 3C. Martín-Santos, C. Jarava-Barrera, S. del Pozo, A. Parra, S. Díaz-Tendero, R. Mas-Ballesté, S. Cabrera, J. Alemán, Angew. Chem. Int. Ed. 2014, 53, 8184; Angew. Chem. 2014, 126, 8323.
- 4R. Kumar, Y. Hoshimoto, E. Tamai, M. Ohashi, S. Ogoshi, Nat. Commun. 2017, 8, 32.
- 5Racemic examples for construction of fused polycycles:
- 5aX. Zhou, Y. Pan, X. Li, Angew. Chem. Int. Ed. 2017, 56, 8163; Angew. Chem. 2017, 129, 8275;
- 5bG. Xu, K. Liu, J. Sun, Org. Lett. 2017, 19, 6440;
- 5cY. Fukui, P. Liu, Q. Liu, Z. He, N. Wu, P. Tian, G.-Q. Lin, J. Am. Chem. Soc. 2014, 136, 15607;
- 5dM. Lin, F. Li, L. Jiao, Z.-X. Yu, J. Am. Chem. Soc. 2011, 133, 1690.
- 6Reviews:
- 6aM. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49;
- 6bV. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. Int. Ed. 2008, 47, 4268; Angew. Chem. 2008, 120, 4338;
- 6cP. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791;
- 6dA. Marinetti, H. Jullien, A. Voituriez, Chem. Soc. Rev. 2012, 41, 4884;
- 6eY. Wang, Z.-X. Yu, Acc. Chem. Res. 2015, 48, 2288;
- 6fY. Shibata, K. Tanaka, Synthesis 2012, 44, 323.
- 7Recent examples:
- 7aJ.-F. Tan, C. T. Bormann, F. G. Perrin, F. M. Chadwick, K. Severin, N. Cramer, J. Am. Chem. Soc. 2019, 141, 10372;
- 7bY. Oonishi, S. Masusaki, S. Sakamoto, Y. Sato, Angew. Chem. Int. Ed. 2019, 58, 8736; Angew. Chem. 2019, 131, 8828;
- 7cC.-H. Liu, Z.-X. Yu, Angew. Chem. Int. Ed. 2017, 56, 8667; Angew. Chem. 2017, 129, 8793;
- 7dC. Zhu, J.-J. Feng, J. Zhang, Angew. Chem. Int. Ed. 2017, 56, 1351; Angew. Chem. 2017, 129, 1371;
- 7eT. Lin, C. Zhu, P. Zhang, Y. Wang, H. Wu, J. Feng, J. Zhang, Angew. Chem. Int. Ed. 2016, 55, 10844; Angew. Chem. 2016, 128, 11002;
- 7fK. Masutomi, H. Sugiyama, H. Uekusa, Y. Shibata, K. Tanaka, Angew. Chem. Int. Ed. 2016, 55, 15373; Angew. Chem. 2016, 128, 15599;
- 7gK. Masutomi, N. Sakiyama, K. Noguchi, K. Tanaka, Angew. Chem. Int. Ed. 2012, 51, 13031; Angew. Chem. 2012, 124, 13208;
- 7hK. Masutomi, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2014, 136, 7627;
- 7iP. A. Inglesby, J. Bacsa, D. E. Negru, P. A. Evans, Angew. Chem. Int. Ed. 2014, 53, 3952; Angew. Chem. 2014, 126, 4033;
- 7jM. Lin, G. Kang, Y. Guo, Z.-X. Yu, J. Am. Chem. Soc. 2012, 134, 398;
- 7kP. A. Evans, P. A. Inglesby, J. Am. Chem. Soc. 2008, 130, 12838;
- 7lK. Tanaka, K. Takeishi, K. Noguchi, J. Am. Chem. Soc. 2006, 128, 4586;
- 7mP. A. Evans, K. W. Lai, J. R. Sawyer, J. Am. Chem. Soc. 2005, 127, 12466;
- 7nT. Shibata, Y. Tahara, K. Tamura, K. Endo, J. Am. Chem. Soc. 2008, 130, 3451;
- 7oK. Tanaka, Y. Otake, H. Sagae, K. Noguchi, M. Hirano, Angew. Chem. Int. Ed. 2008, 47, 1312; Angew. Chem. 2008, 120, 1332.
- 8
- 8aX.-P. Zeng, Z.-Y. Cao, Y.-H. Wang, F. Zhou, J. Zhou, Chem. Rev. 2016, 116, 7330;
- 8bC.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 12662; Angew. Chem. 2012, 124, 12834;
- 8cJ.-W. Park, Z. Chen, V. M. Dong, J. Am. Chem. Soc. 2016, 138, 3310;
- 8dJ.-W. Park, K. G. M. Kou, D. K. Kim, V. M. Dong, Chem. Sci. 2015, 6, 4479;
- 8eD. Qian, M. Chen, A. C. Bissember, J. Sun, Angew. Chem. Int. Ed. 2018, 57, 3763; Angew. Chem. 2018, 130, 3825.
- 9
- 9aC. Duan, Y. Tan, J. Zhang, S. Yang, H. Dong, P. Tian, G.-Q. Lin, Org. Lett. 2019, 21, 1690;
- 9bQ. Teng, N. Thirupathi, C.-H. Tung, Z. Xu, Chem. Sci. 2019, 10, 6863.
- 10Desymmetric reaction to bicyclic hydrobenzofurans:
- 10aQ. Gu, S.-L. You, Chem. Sci. 2011, 2, 1519;
- 10bQ. Gu, Z.-Q. Rong, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2010, 132, 4056;
- 10cZ.-T. He, B. Tian, Y. Fukui, X. Tong, P. Tian, G.-Q. Lin, Angew. Chem. Int. Ed. 2013, 52, 5314; Angew. Chem. 2013, 125, 5422;
- 10dZ.-T. He, X.-Q. Tang, L.-B. Xie, M. Cheng, P. Tian, G.-Q. Lin, Angew. Chem. Int. Ed. 2015, 54, 14815; Angew. Chem. 2015, 127, 15028;
- 10eX. Su, W. Zhou, Y. Li, J. Zhang, Angew. Chem. Int. Ed. 2015, 54, 6874; Angew. Chem. 2015, 127, 6978;
- 10fW. Yao, X. Dou, S. Wen, J. Wu, J. J. Vittal, Y. Lu, Nat. Commun. 2016, 7, 13024;
- 10gJ. Chen, X. Han, X. Lu, Angew. Chem. Int. Ed. 2017, 56, 14698; Angew. Chem. 2017, 129, 14890;
- 10hK. K. Gollapelli, S. Donikela, N. Manjula, R. Chegondi, ACS Catal. 2018, 8, 1440;
- 10iT. Shu, L. Zhao, S. Li, X.-Y. Chen, C. von Essen, K. Rissanen, D. Enders, Angew. Chem. Int. Ed. 2018, 57, 10985; Angew. Chem. 2018, 130, 11151.
- 11CCDC 1938461 (3 a), 1943438 (4 ai), 1915702 (6 a) and 1915701 (9) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
- 12De novo construction of benzene:
- 12aZ. Lu, Y. Li, J. Deng, A. Li, Nat. Chem. 2013, 5, 679;
- 12bJ. Li, P. Yang, M. Yao, J. Deng, A. Li, J. Am. Chem. Soc. 2014, 136, 16477.
Citing Literature
February 3, 2020
Pages 2220-2224