Bimetallic Rhodium(II)/Indium(III) Relay Catalysis for Tandem Insertion/Asymmetric Claisen Rearrangement
Yushuang Chen
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Dr. Shunxi Dong
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorXi Xu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Dr. Xiaohua Liu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaoming Feng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorYushuang Chen
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Dr. Shunxi Dong
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorXi Xu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Dr. Xiaohua Liu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaoming Feng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorGraphical Abstract
A highly efficient asymmetric tandem reaction of N-sulfonyl-1,2,3-triazoles with two types of allyl alcohol esters was achieved by using a bimetallic rhodium(II)/chiral N,N′-dioxide–indium(III) complex catalyst. A series of β/γ-amino acid derivatives bearing different substituents were obtained in a good to excellent diastereo- and enantioselective manner.
Abstract
The first example of catalytic insertion/asymmetric Claisen rearrangement tandem reaction of N-sulfonyl-1,2,3-triazoles with allyl alcohol esters was achieved by bimetallic relay catalytic systems involving achiral rhodium salt and chiral N,N′-dioxide–indium(III) complex. This manifold could overcome the limitation of single RhII catalysis, providing a straight and facile route to various enantioenriched β/γ-amino acid derivatives in high yields (up to 99 %) with excellent diastereo- and enantioselectivities (up to >95:5 dr, 98:2 er). Moreover, possible transition state models were proposed to elucidate the origin of chiral induction based on the control experiments and X-ray crystal structure of the catalyst.
Supporting Information
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References
- 1For selected reviews on the asymmetric reactions of metal carbenes derived from diazo compounds, see:
- 1aH. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861;
- 1bM. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704;
- 1cS.-F. Zhu, Q.-L. Zhou, Acc. Chem. Res. 2012, 45, 1365;
- 1dH. M. L. Davies, Y. J. Lian, Acc. Chem. Res. 2012, 45, 923;
- 1eX. Guo, W. H. Hu, Acc. Chem. Res. 2013, 46, 2427;
- 1fS. Chanthamath, S. Iwasa, Acc. Chem. Res. 2016, 49, 2080;
- 1gY. Xia, D. Qiu, J. B. Wang, Chem. Rev. 2017, 117, 13810.
- 2For selected examples on the asymmetric reactions of metal carbenes derived from diazo compounds, see:
- 2aG. A. Moniz, J. L. Wood, J. Am. Chem. Soc. 2001, 123, 5095;
- 2bZ. J. Li, H. M. L. Davies, J. Am. Chem. Soc. 2010, 132, 396;
- 2cS.-F. Zhu, Y. Cai, H.-X. Mao, J.-H. Xie, Q.-L. Zhou, Nat. Chem. 2010, 2, 546;
- 2dZ. J. Li, V. Boyarskikh, J. H. Hansen, J. Autschbach, D. G. Musaev, H. M. L. Davies, J. Am. Chem. Soc. 2012, 134, 15497;
- 2eX. C. Xu, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2013, 135, 12439;
- 2fZ. K. Zhang, Z. Sheng, W. Z. Yu, G. J. Wu, R. Zhang, W. D. Chu, Y. Zhang, J. B. Wang, Nat. Chem. 2017, 9, 970;
- 2gX. B. Lin, Y. Tang, W. Yang, F. Tan, L. L. Lin, X. H. Liu, X. M. Feng, J. Am. Chem. Soc. 2018, 140, 3299.
- 3
- 3aS. Chuprakov, F. W. Hwang, V. Gevorgyan, Angew. Chem. Int. Ed. 2007, 46, 4757; Angew. Chem. 2007, 119, 4841;
- 3bB. Chattopadhyay, V. Gevorgyan, Angew. Chem. Int. Ed. 2012, 51, 862; Angew. Chem. 2012, 124, 886;
- 3cY. Shi, A. V. Gulevich, V. Gevorgyan, Angew. Chem. Int. Ed. 2014, 53, 14191; Angew. Chem. 2014, 126, 14415;
- 3dJ. H. Kim, T. Gensch, D. B. Zhao, L. Stegemann, C. A. Strassert, F. Glorius, Angew. Chem. Int. Ed. 2015, 54, 10975; Angew. Chem. 2015, 127, 11126;
- 3eA. Joshi, D. C. Mohan, S. Adimurthy, Org. Lett. 2016, 18, 464.
- 4
- 4aH. M. L. Davies, J. S. Alford, Chem. Soc. Rev. 2014, 43, 5151;
- 4bP. Anbarasan, D. Yadagiri, S. Rajasekar, Synthesis 2014, 46, 3004;
- 4cY. Jiang, R. Sun, X. Y. Tang, M. Shi, Chem. Eur. J. 2016, 22, 17910;
- 4dT. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972;
- 4eT. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194;
- 4fS. Y. Liu, W. F. Yao, Y. Liu, Q. H. Wei, J. H. Chen, X. Wu, F. Xia, W. H. Hu, Sci. Adv. 2017, 3, e 1602467.
- 5T. Nakamuro, K. Hagiwara, T. Miura, M. Murakami, Angew. Chem. Int. Ed. 2018, 57, 5497; Angew. Chem. 2018, 130, 5595.
- 6
- 6aT. Miura, T. Tanaka, T. Biyajima, A. Yada, M. Murakami, Angew. Chem. Int. Ed. 2013, 52, 3883; Angew. Chem. 2013, 125, 3975;
- 6bT. Miura, T. Tanaka, K. Matsumoto, M. Murakami, Chem. Eur. J. 2014, 20, 16078;
- 6cD. J. Jung, H. J. Jeon, J. H. Lee, S.-g. Lee, Org. Lett. 2015, 17, 3498;
- 6dH. J. Jeon, M. S. Kwak, D. J. Jung, J. Bouffard, S.-g. Lee, Org. Biomol. Chem. 2016, 14, 11238;
- 6eT. Miura, T. Tanaka, Q. Zhao, S. G. Stewart, M. Murakami, Helv. Chim. Acta. 2017, 100, e 1600320;
- 6fD. Yadagiri, P. Anbarasan, Chem. Eur. J. 2013, 19, 15115;
- 6gT. Miura, T. Tanaka, A. Yada, M. Murakami, Chem. Lett. 2013, 42, 1308.
- 7For selected examples on the asymmetric reactions of 1,2,3-triazoles, see:
- 7aS. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034;
- 7bN. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 2510;
- 7cT. Miura, T. Nakamuro, H. Nikishima, M. Murakami, Chem. Lett. 2016, 45, 1003;
- 7dS. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352;
- 7eR. W. Kubiak II, J. D. Mighion, S. M. Wilkerson-Hill, J. S. Alford, T. Yoshidomi, H. M. L. Davies, Org. Lett. 2016, 18, 3118;
- 7fJ. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802;
- 7gM. Zibinsky, V. V. Fokin, Angew. Chem. Int. Ed. 2013, 52, 1507; Angew. Chem. 2013, 125, 1547;
- 7hR. W. Kubiak II, H. M. L. Davies, Org. Lett. 2018, 20, 3771.
- 8
- 8aM. Seki, T. Shimizu, K. Matsumoto, J. Org. Chem. 2000, 65, 1298;
- 8bA. E. Taggi, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10;
- 8cA. R. Katritzky, H. Tao, R. Jiang, K. Suzuki, K. Kirichenko, J. Org. Chem. 2007, 72, 407;
- 8dK. K. Zhang, X. P. Liang, M. He, J. Wu, Y. P. Zhang, W. Xue, L. H. Jin, S. Yang, D. Y. Hu, Molecules 2013, 18, 6142.
- 9
- 9aX. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44, 574;
- 9bX. H. Liu, L. L. Lin, X. M. Feng, Org. Chem. Front. 2014, 1, 298;
- 9cX. H. Liu, H. F. Zheng, Y. Xia, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2017, 50, 2621;
- 9dX. H. Liu, S. X. Dong, L. L. Lin, X. M. Feng, Chin. J. Chem. 2018, 36, 791;
- 9eX. M. Feng, Z. Wang, X. H. Liu, Top. Organomet. Chem. 2018, 62, 147.
- 10
- 10aJ. Li, L. L. Lin, B. W. Hu, X. J. Lian, G. Wang, X. H. Liu, X. M. Feng, Angew. Chem. Int. Ed. 2016, 55, 6075; Angew. Chem. 2016, 128, 6179;
- 10bJ. Li, L. L. Lin, B. W. Hu, P. F. Zhou, T. Y. Huang, X. H. Liu, X. M. Feng, Angew. Chem. Int. Ed. 2017, 56, 885; Angew. Chem. 2017, 129, 903;
- 10cT. Y. Huang, X. H. Liu, J. W. Lang, J. Xu, L. L. Lin, X. M. Feng, ACS Catal. 2017, 7, 5654;
- 10dD. Zhang, L. L. Lin, J. Yang, X. H. Liu, X. M. Feng, Angew. Chem. Int. Ed. 2018, 57, 12323; Angew. Chem. 2018, 130, 12503;
- 10eB. W. Hu, J. Li, W. D. Cao, Q. C. Lin, J. Yang, L. L. Lin, X. H. Liu, X. M. Feng, Adv. Synth. Catal. 2018, 360, 2831;
- 10fJ. Yang, C. Q. Ke, D. Zhang, X. H. Liu, X. M. Feng, Org. Lett. 2018, 20, 4536.
- 11
- 11aA. M. Martín Castro, Chem. Rev. 2004, 104, 2939;
- 11bE. A. Ilardi, C. E. Stivala, A. Zakarian, Chem. Soc. Rev. 2009, 38, 3133;
- 11cY. B. Liu, X. H. Liu, H. P. Hu, J. Guo, Y. Xia, L. L. Lin, X. M. Feng, Angew. Chem. Int. Ed. 2016, 55, 4054; Angew. Chem. 2016, 128, 4122;
- 11dH. F. Zheng, Y. Wang, C. R. Xu, X. Xu, L. L. Lin, X. H. Liu, X. M. Feng, Nat. Commun. 2018, 9, 1968.
- 12Several rhodium sources were tested, and Rh2(esp)2 was shown to be the most efficient one (Table S1 in the Supporting Information).
- 13With In(OTf)3 as the central metal, selected chiral N,N′-dioxide ligands were also investigated, no better results were obtained.
- 14CCDC 1846270, 1846269, and 1866880 (3 ab, 3 ag, and [L3-TQ-(S)-EPh/In(OTf)3]) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
- 15
- 15aK. M. Osten, P. Mehrkhodavandi, Acc. Chem. Res. 2017, 50, 2861;
- 15bI. Yu, A. Acosta-Ramírez, P. Mehrkhodavandi, J. Am. Chem. Soc. 2012, 134, 12758;
- 15cA. Acosta-Ramírez, A. F. Douglas, I. Yu, B. O. Patrick, P. L. Diaconescu, P. Mehrkhodavandi, Inorg. Chem. 2010, 49, 5444;
- 15dA. F. Douglas, B. O. Patrick, P. Mehrkhodavandi, Angew. Chem. Int. Ed. 2008, 47, 2290; Angew. Chem. 2008, 120, 2322.
