Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols†
Dr. Debasis Banerjee
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorDr. Kathrin Junge
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Debasis Banerjee
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorDr. Kathrin Junge
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorThis research has been funded by the State of Mecklenburg–Western Pomerania, the BMBF, and the DFG (Leibniz Prize). We thank Dr. W. Baumann, Dr. C. Fischer, S. Buchholz, S. Schareina, A. Koch, and S. Rossmeisl (all at LIKAT) for their excellent technical and analytical support.
Abstract
Cooperative catalysis by [Pd(dba)2] and the chiral phosphoric acid BA1 in combination with the phosphoramidite ligand L8 enabled the efficient enantioselective amination of racemic allylic alcohols with a variety of functionalized amines. This catalytic protocol is highly regio- and stereoselective (up to e.r. 96:4) and furnishes valuable chiral amines in almost quantitative yield.
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_201405511_sm_miscellaneous_information.pdf4.1 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
- 1
- 1aB. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
- 1bB. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
- 1cZ. Lu, S.-M. Ma, Angew. Chem. Int. Ed. 2008, 47, 258; Angew. Chem. 2008, 120, 264.
- 2For selected examples of palladium-catalyzed allylic substitution reactions, see:
- 2aB. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
- 2bS. Yasuda, N. Kumagai, M. Shibasaki, Heterocycles 2012, 86, 745;
- 2cJ. Ye, J. Zhao, J. Xu, Y. Mao, Y. J. Zhang, Chem. Commun. 2013, 49, 9761;
- 2dY.-X. Li, Q.-Q. Xuan, L. Liu, D. Wang, Y. J. Chen, C. J. Li, J. Am. Chem. Soc. 2013, 135, 12536;
- 2eZ. L. Tao, W.-Q. Zhang, D.-F. Chen, A. Adele, L.-Z. Gong, J. Am. Chem. Soc. 2013, 135, 9255.
- 3For selected examples of allylic amination reactions, see:
- 3aX. Wang, F. Meng, Y. Wang, Z. Han, Y.-J. Chen, L. Liu, Z. Wang, K. Ding, Angew. Chem. Int. Ed. 2012, 51, 9276; Angew. Chem. 2012, 124, 9410;
- 3bX. Wang, P. Guo, Z. Han, X. Wang, Z. Wang, K. Ding, J. Am. Chem. Soc. 2014, 136, 405;
- 3cJ. W. Faller, J. C. Wilt, Org. Lett. 2005, 7, 633;
- 3dY. Uozumi, H. Tanaka, K. Shibatomi, Org. Lett. 2004, 6, 281;
- 3eX. L. Hou, B. H. Zheng, Org. Lett. 2009, 11, 1789;
- 3fT. Hayashi, K. Kishi, A. Yamamoto, Y. Ito, Tetrahedron Lett. 1990, 31, 1743;
- 3gS.-L. You, X.-Z. Zhu, Y.-M. Luo, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2001, 123, 7471;
- 3hB. M. Trost, S. Malhotra, D. E. Olson, A. Maruniak, J. D. Bois, J. Am. Chem. Soc. 2009, 131, 4190; for the enantioselective amination of alcohols, see:
- 3iY. Zhang, C.-S. Lim, D. S. B. Sim, H.-J. Pan, Y. Zhao, Angew. Chem. Int. Ed. 2014, 53, 1399; Angew. Chem. 2014, 126, 1423.
- 4
- 4aM. Bandini, Angew. Chem. Int. Ed. 2011, 50, 994; Angew. Chem. 2011, 123, 1026;
- 4bM. Bandini, G. Cera, M. Chiarucci, Synthesis 2012, 504;
- 4cB. Sundararaju, M. Achard, C. Bruneau, Chem. Soc. Rev. 2012, 41, 4467;
- 4dM. Raducan, R. Alam, K. J. Szabó, Angew. Chem. Int. Ed. 2012, 51, 13050; Angew. Chem. 2012, 124, 13227.
- 5
- 5aJ. Clark, Green Chem. 1999, 1, 1;
- 5bR. A. Sheldon, Green Chem. 2008, 10, 359;
- 5cM. Beller, G. Centi, ChemSusChem 2009, 2, 459;
- 5dB. M. Trost, Science 1991, 254, 1471.
- 6
- 6aS.-C. Yang, Y.-C. Hus, K.-H. Gan, Tetrahedron 2006, 62, 3949, and references therein;
- 6bI. Starý, I. G. Stara, P. Kocovsky, Tetrahedron Lett. 1993, 34, 179;
- 6cY. Tamaru, Eur. J. Org. Chem. 2005, 2647;
- 6dK. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241;
- 6eS. C. Yang, C. W. Hung, Synthesis 1999, 1747;
- 6fN. T. Patil, Y. Yamamoto, Tetrahedron Lett. 2004, 45, 3101;
- 6gM. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065;
- 6hS. C. Yang, C. W. Hung, J. Org. Chem. 1999, 64, 5000.
- 7Y. Yamashita, A. Gopalarathnam, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7508.
- 8
- 8aC. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. Int. Ed. 2007, 46, 3139; Angew. Chem. 2007, 119, 3200;
- 8bM. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. Int. Ed. 2012, 51, 3470; Angew. Chem. 2012, 124, 3527.
- 9
- 9aD. Hollmann, S. Bähn, A. Tillack, M. Beller, Angew. Chem. Int. Ed. 2007, 46, 8291; Angew. Chem. 2007, 119, 8440;
- 9bS. Imm, S. Bähn, L. Neubert, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2010, 49, 8126; Angew. Chem. 2010, 122, 8303;
- 9cS. Imm, S. Bähn, M. Zhang, L. Neubert, H. Neumann, F. Klasovsky, J. Pfeffer, T. Hass, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 7599; Angew. Chem. 2011, 123, 7741;
- 9dD. Banerjee, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, ChemSusChem 2012, 5, 2039;
- 9eD. Banerjee, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, Angew. Chem. Int. Ed. 2012, 51, 11556; Angew. Chem. 2012, 124, 11724.
- 10
- 10aA. Tillack, V. Khedkar, H. Jiao, M. Beller, Eur. J. Org. Chem. 2005, 5001;
- 10bA. Tillack, H. Jiao, C.-I. Garcia, C. G. Hartung, M. Beller, Chem. Eur. J. 2004, 10, 2409;
- 10cK. Alex, A. Tillack, N. Schwarz, M. Beller, ChemSusChem 2008, 1, 333;
- 10dD. Banerjee, K. Junge, M. Beller, Angew. Chem. Int. Ed. 2014, 53, 1630; Angew. Chem. 2014, 126, 1656;
- 10eD. Banerjee, K. Junge, M. Beller, Org. Chem. Front. 2014, 1, 368.
- 11When amination reactions are performed with phosphoramidite ligands, the presence of heteroatoms facilitates the partial activation of the hydroxy group of the allylic alcohol through strong hydrogen bonding, albeit with lower product yields; for details, see: Y. Gumrukcu, B. de Bruin, J. N. H. Reek, ChemSusChem 2014, 7, 890; for selected reviews of phosphoramidite ligands, see:
- 11aB. L. Feringa, Acc. Chem. Res. 2000, 33, 346;
- 11bJ. F. Teichert, B. L. Feringa, Angew. Chem. Int. Ed. 2010, 49, 2486; Angew. Chem. 2010, 122, 2538;
- 11cH. W. Lam, Synthesis 2011, 2011.
- 12
- 12aG.-X. Jiang, B. List, Angew. Chem. Int. Ed. 2011, 50, 9471; Angew. Chem. 2011, 123, 9643;
- 12bM. Mahlau, B. List, Angew. Chem. Int. Ed. 2013, 52, 518; Angew. Chem. 2013, 125, 540.
- 13For recent reviews, see:
- 13aA. Grossmann, D. Enders, Angew. Chem. Int. Ed. 2012, 51, 314; Angew. Chem. 2012, 124, 320;
- 13bP. de Armas, D. Tejedor, F. García-Tellado, Angew. Chem. Int. Ed. 2010, 49, 1013; Angew. Chem. 2010, 122, 1029;
- 13cC. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999;
- 13dN. T. Patil, V. S. Shinde, B. Gajula, Org. Biomol. Chem. 2012, 10, 211;
- 13eZ.-T. Du, Z.-H. Shao, Chem. Soc. Rev. 2013, 42, 1337.
- 14Prolongation of the reaction time leads to racemization and isomerization of the desired allylic amine products; for details, see:
- 14aX. Zhao, D. Liu, H. Guo, Y. Liu, W. Zhang, J. Am. Chem. Soc. 2011, 133, 19354;
- 14bI. Dubovyk, D. Pichugin, A. K. Yudin, Angew. Chem. Int. Ed. 2011, 50, 5924; Angew. Chem. 2011, 123, 6046.
- 15B. M. Trost, P. E. Strege, L. Weber, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3407.
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.