Nickel(II)-Catalyzed Asymmetric Propargyl and Allyl Claisen Rearrangements to Allenyl- and Allyl-Substituted β-Ketoesters†
Yangbin Liu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorHaipeng Hu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorHaifeng Zheng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorYong Xia
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 authorDr. Lili Lin
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)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)Search for more papers by this authorYangbin Liu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorHaipeng Hu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorHaifeng Zheng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
Search for more papers by this authorYong Xia
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 authorDr. Lili Lin
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)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)Search for more papers by this authorWe thank the National Basic Research Program of China (973 Program: 2011CB808600), the National Natural Science Foundation of China (21290182, 21321061 and 21172151), and the Ministry of Education (20110181130014) for financial support.
Abstract
Highly efficient catalytic asymmetric Claisen rearrangements of O-propargyl β-ketoesters and O-allyl β-ketoesters have been accomplished under mild reaction conditions. In the presence of the chiral N,N′-dioxide/NiII complex, a wide range of allenyl/allyl-substituted all-carbon quaternary β-ketoesters was obtained in generally good yield (up to 99 %) and high diastereoselectivity (up to 99:1 d.r.) with excellent enantioselectivity (up to 99 % ee).
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 |
|---|---|
| ange_201404643_sm_miscellaneous_information.pdf9.9 MB | miscellaneous_information |
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 recent reviews, see;
- 1aH. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43;
- 1bM. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461;
- 1cU. Nubbemeyer, Synthesis 2003, 961;
- 1dA. M. Martín Castro, Chem. Rev. 2004, 104, 2939;
- 1e The Claisen Rearrangment (Eds.: ), Wiley-VCH, Weinheim, 2007;
- 1fE. A. Ilardi, C. E. Stivala, A. Zakarian, Chem. Soc. Rev. 2009, 38, 3133;
- 1gJ. Rehbein, M. Hiersemann, Synthesis 2013, 1121.
- 2
- 2aL. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835;
10.1002/1521-3757(20011217)113:24<4835::AID-ANGE4835>3.0.CO;2-D Google ScholarAngew. Chem. Int. Ed. 2001, 40, 4700;10.1002/1521-3773(20011217)40:24<4700::AID-ANIE4700>3.0.CO;2-6 CAS PubMed Web of Science® Google Scholar
- 2bL. Abraham, M. Körner, P. Schwab, M. Hiersemann, Adv. Synth. Catal. 2004, 346, 1281;
- 2cL. Abraham, M. Körner, M. Hiersemann, Tetrahedron Lett. 2004, 45, 3647;
- 2dJ. Troendlin, J. Rehbein, M. Hiersemann, O. Trapp, J. Am. Chem. Soc. 2011, 133, 16444;
- 2eJ. Tan, C. H. Cheon, H. Yamamoto, Angew. Chem. 2012, 124, 8389; Angew. Chem. Int. Ed. 2012, 51, 8264.
- 3
- 3aC. Uyeda, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 9228;
- 3bC. Uyeda, A. R. Rötheli, E. N. Jacobsen, Angew. Chem. 2010, 122, 9947;
10.1002/ange.201005183 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 9753.
- 4
- 4aJ. Kaeobamrung, J. Mahatthananchai, P. Zheng, J. W. Bode, J. Am. Chem. Soc. 2010, 132, 8810;
- 4bL. Candish, D. W. Lupton, J. Am. Chem. Soc. 2013, 135, 58.
- 5
- 5aM. E. Geherty, R. D. Dura, S. G. Nelson, J. Am. Chem. Soc. 2010, 132, 11875;
- 5bE. C. Linton, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 16162.
- 6For reviews on propargyl Claisen rearrangement, see:
- 6aD. Tejedor, G. Méndez-Abt, L. Cotos, F. García-Tellado, Chem. Soc. Rev. 2013, 42, 458. For selected examples of propargyl rearrangement in organic synthesis, see:
- 6bA. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. 2007, 119, 4005; Angew. Chem. Int. Ed. 2007, 46, 3931;
- 6cP. Mauleón, J. L. Krinsky, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 4513;
- 6dK. Tanaka, E. Okazaki, Y. Shibata, J. Am. Chem. Soc. 2009, 131, 10822;
- 6eH. Cao, H. Jiang, W. Yao, X. Liu, Org. Lett. 2009, 11, 1931;
- 6fH. Jiang, W. Yao, H. Cao, H. Huang, D. Cao, J. Org. Chem. 2010, 75, 5347;
- 6gA. Gille, J. Rehbein, M. Hiersemann, Org. Lett. 2011, 13, 2122;
- 6hE. Okazaki, R. Okamoto, Y. Shibata, K. Noguchi, K. Tanaka, Angew. Chem. 2012, 124, 6826;
10.1002/ange.201202125 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 6722;
- 6iY. Xiong, S. E. Schaus, J. A. Porco, Jr., Org. Lett. 2013, 15, 1962.
- 7For reviews on allenes in organic synthesis, see:
- 7aS. Ma, Acc. Chem. Res. 2003, 36, 701;
- 7bA. Hoffmann-Röder, N. Krause, Angew. Chem. 2004, 116, 1216;
10.1002/ange.200300628 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1196;
- 7cN. Krause, A. S. K. Hashimi, Modern Allene Chemistry, Wiley-VCH, Weinheim, 2004;
- 7dS. Ma, Chem. Rev. 2005, 105, 2829;
- 7eB. J. Cowen, S. J. Miller, Chem. Soc. Rev. 2009, 38, 3102;
- 7fC. Aubert, L. Fensterbank, P. Garcia, M. Malacria, A. Simonneau, Chem. Rev. 2011, 111, 1954;
- 7gS. Yu, S. Ma, Angew. Chem. 2012, 124, 3128; Angew. Chem. Int. Ed. 2012, 51, 3074;
- 7hJ. Ye, S. Ma, Acc. Chem. Res. 2014, 47, 989.
- 8For selected examples of auxiliary controlled diastereoselective versions, see:
- 8aM. O. Frederick, R. P. Hsung, R. H. Lambeth, J. A. Mulder, M. R. Tracey, Org. Lett. 2003, 5, 2663;
- 8bK. C. M. Kurtz, M. O. Frederick, R. H. Lambeth, J. A. Mulder, M. R. Tracey, R. P. Hsung, Tetrahedron 2006, 62, 3928.
- 9For selected examples of optical propargyl alcohols, see:
- 9aB. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 15978;
- 9bB. D. Sherry, L. Maus, B. N. Laforteza, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 8132;
- 9cR. A. Brawn, J. S. Panek, Org. Lett. 2007, 9, 2689;
- 9dY. Tang, L. Shen, B. J. Dellaria, R. P. Hsung, Tetrahedron Lett. 2008, 49, 6404;
- 9eB. Lü, X. Jiang, C. Fu, S. Ma, J. Org. Chem. 2009, 74, 438.
- 10
- 10aT. Cao, J. Deitch, E. C. Linton, M. C. Kozlowski, Angew. Chem. 2012, 124, 2498; Angew. Chem. Int. Ed. 2012, 51, 2448;
- 10bT. Cao, E. C. Linton, J. Deitch, S. Berritt, M. C. Kozlowski, J. Org. Chem. 2012, 77, 11034.
- 11K. C. K. Swamy, N. N. B. Kumar, E. Balaraman, K. V. P. P. Kumar, Chem. Rev. 2009, 109, 2551.
- 12When the ester group was replaced with CH2OTBS, the rearrangement product was obtained only in less 20 % yield and 3 % ee under the optimized reaction conditions.
- 13For reviews, see:
- 13aX. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44, 574;
- 13bX. H. Liu, L. L. Lin, X. M. Feng, Org. Chem. Front. 2014, 1, 298; For recent examples, see:
- 13cW. D. Cao, X. H. Liu, R. X. Peng, P. He, L. L. Lin, X. M. Feng, Chem. Commun. 2013, 49, 3470;
- 13dM. S. Xie, X. H. Liu, X. X. Wu, Y. F. Cai, L. L. Lin, X. M. Feng, Angew. Chem. 2013, 125, 5714; Angew. Chem. Int. Ed. 2013, 52, 5604;
- 13eW. Li, X. H. Liu, F. Tan, X. Y. Hao, J. F. Zheng, L. L. Lin, X. M. Feng, Angew. Chem. 2013, 125, 11083; Angew. Chem. Int. Ed. 2013, 52, 10883;
- 13fK. Zheng, L. L. Lin, X. M. Feng, Acta Chim. Sinica 2012, 70, 1785;
- 13gM. S. Xie, X. X. Wu, G. Wang, L. L. Lin, X. M. Feng, Acta Chim. Sinica 2014, 72, 856.
- 14CCDC 995994 (2 j) 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.
- 15The NO2 group was introduced for the other substrates that could not be synthesized according to the general method.
- 16J. J. Gajewski, Acc. Chem. Res. 1997, 30, 219.
- 17K. Zheng, X. H. Liu, J. N. Zhao, Y. Yang, L. L. Lin, X. M. Feng, Chem. Commun. 2010, 46, 3771.
- 18The steric hindrance between the propargyl unit and the bulky aniline moiety of ligand might be disfavor for the enantioselective reaction, as shown in the lower right model.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
