Portal de Periódicos da CAPES

Organocatalytic Asymmetric Inverse‐Electron‐Demand Aza‐Diels–Alder Reaction of N ‐Sulfonyl‐1‐aza‐1,3‐butadienes and Aldehydes

2008; Wiley; Volume: 120; Issue: 51 Linguagem: Inglês

10.1002/ange.200804183

1521-3757

Bo Han, Jun‐Long Li, Chao Ma, Shanjun Zhang, Ying‐Chun Chen,

Chemical Synthesis and Analysis

Angewandte ChemieVolume 120, Issue 51 p. 10119-10122 Zuschrift Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels–Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes Bo Han, Bo Han Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorJun-Long Li, Jun-Long Li Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorChao Ma, Chao Ma Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorShan-Jun Zhang, Shan-Jun Zhang Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorYing-Chun Chen Prof. Dr., Ying-Chun Chen Prof. Dr. [email protected] Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609 State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)Search for more papers by this author Bo Han, Bo Han Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorJun-Long Li, Jun-Long Li Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorChao Ma, Chao Ma Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorShan-Jun Zhang, Shan-Jun Zhang Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609Search for more papers by this authorYing-Chun Chen Prof. Dr., Ying-Chun Chen Prof. Dr. [email protected] Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609 State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)Search for more papers by this author First published: 03 December 2008 https://doi.org/10.1002/ange.200804183Citations: 69Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Wasser ist entscheidend, um die Titelreaktion in Gegenwart des α,α-Diphenylprolinols 1 mit hohen Umsätzen ablaufen zu lassen. Ein breites Spektrum an Substraten wurde mit sehr guten Stereoselektivitäten umgesetzt (TMS=Trimethylsilyl, Tos=p-Toluolsulfonyl). Die entstehenden Halbaminale konnten in eine Vielzahl chiraler Piperidine und andere wertvolle Verbindungen überführt werden. 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 ange_200804183_sm_miscellaneous_information.pdf3.5 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 a review, see: M. Rubiralta, E. Giralt, A. Diez, Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and Its Derivatives, Elsevier, Amsterdam, 1991. Google Scholar 2For selected examples of ADAR of imines, see: Google Scholar 2aS. Yao, S. Saaby, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2000, 6, 2435; 10.1002/1521-3765(20000703)6:13 3.0.CO;2-Z CASPubMedWeb of Science®Google Scholar 2bN. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018; 10.1021/ja030033p CASPubMedWeb of Science®Google Scholar 2cO. Garcia Mancheno, R. Gomez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2004, 126, 456; 10.1021/ja038494y CASPubMedWeb of Science®Google Scholar 2dS. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, Y. Yamashita, Proc. Natl. Acad. Sci. USA 2004, 101, 5476; 10.1073/pnas.0307870101 CASPubMedWeb of Science®Google Scholar 2eV. Jurčík, K. Arai, M. M. Salter, Y. Yamashita, S. Kobayashi, Adv. Synth. Catal. 2008, 350, 647; 10.1002/adsc.200700615 CASWeb of Science®Google Scholar 2fT. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070; 10.1021/ja064676r CASPubMedWeb of Science®Google Scholar 2gJ. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914; 10.1002/ange.200601345 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 4796; 10.1002/anie.200601345 CASPubMedWeb of Science®Google Scholar 2hM. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996; 10.1002/ange.200603199 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 7832; 10.1002/anie.200603199 CASPubMedWeb of Science®Google Scholar 2iH. Liu, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Org. Lett. 2006, 8, 6023. 10.1021/ol062499t CASPubMedWeb of Science®Google Scholar 3For selected catalytic cascade reactions to access chiral piperidine derivatives, see: Google Scholar 3aM. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 5920; 10.1002/ange.200801435 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 5836; 10.1002/anie.200801435 CASPubMedWeb of Science®Google Scholar 3bJ. Jiang, J. Yu, X.-X. Sun, Q.-Q. Rao, L.-Z. Gong, Angew. Chem. 2008, 120, 2492; 10.1002/ange.200705300 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 2458; 10.1002/anie.200705300 CASPubMedWeb of Science®Google Scholar 3cL. Zu, H. Xie, H. Li, J. Wang, X. Yu, W. Wang, Chem. Eur. J. 2008, 14, 6333; 10.1002/chem.200800829 CASPubMedWeb of Science®Google Scholar 3dM. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336; 10.1021/ja0739584 CASPubMedWeb of Science®Google Scholar 3eY. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076; 10.1002/ange.200800662 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4012. 10.1002/anie.200800662 CASPubMedWeb of Science®Google Scholar 4 4aD. L. Boger, A. M. Kasper, J. Am. Chem. Soc. 1989, 111, 1517; 10.1021/ja00186a067 CASWeb of Science®Google Scholar 4bD. L. Boger, W. L. Corbett, J. M. Wiggins, J. Org. Chem. 1990, 55, 2999; 10.1021/jo00297a006 CASWeb of Science®Google Scholar 4cD. L. Boger, W. L. Corbett, T. T. Curran, A. M. Kasper, J. Am. Chem. Soc. 1991, 113, 1713; 10.1021/ja00005a040 CASWeb of Science®Google Scholar 4dD. L. Boger, K. C. Cassidy, S. Nakahara, J. Am. Chem. Soc. 1993, 115, 10733; 10.1021/ja00076a035 CASWeb of Science®Google Scholar 4eJ. Hong, D. L. Boger, J. Am. Chem. Soc. 1998, 120, 1218; 10.1021/ja980775w CASWeb of Science®Google Scholar 4fM. J. Schnermann, D. L. Boger, J. Am. Chem. Soc. 2005, 127, 15704; 10.1021/ja055041f CASPubMedWeb of Science®Google Scholar 4gfor a review on the ADAR of 1-azadienes, see: M. Behforouz, M. Ahmadian, Tetrahedron 2000, 56, 5259. 10.1016/S0040-4020(00)00259-3 CASWeb of Science®Google Scholar 5For selected examples of diastereoselective ADARs of 1-azadienes, see: Google Scholar 5aC. R. Berry, R. P. Hsung, Tetrahedron 2004, 60, 7629; 10.1016/j.tet.2004.05.117 CASWeb of Science®Google Scholar 5bJ. E. Tarver, Jr., K. M. Terranova, M. M. Joullié, Tetrahedron 2004, 60, 10277; 10.1016/j.tet.2004.08.089 CASWeb of Science®Google Scholar 5cR. C. Clark, S. S. Pfeiffer, D. L. Boger, J. Am. Chem. Soc. 2006, 128, 2587. 10.1021/ja0571646 CASPubMedWeb of Science®Google Scholar 6M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418. 10.1021/ja062707c CASPubMedWeb of Science®Google Scholar 7J. Esquivias, R. Gómez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2007, 129, 1480. 10.1021/ja0658766 CASPubMedWeb of Science®Google Scholar 8 8aK. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; 10.1002/ange.200250652 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 1498; 10.1002/anie.200250652 CASPubMedWeb of Science®Google Scholar 8bS. Samanta, J. Krause, T. Mandal, C.-G. Zhao, Org. Lett. 2007, 9, 2745; 10.1021/ol071097y CASPubMedWeb of Science®Google Scholar 8cJ. Wang, F. Yu, X. Zhang, D. Ma, Org. Lett. 2008, 10, 2561; 10.1021/ol800835m CASPubMedWeb of Science®Google Scholar 8dH. Xie, L. Zu, H. R. Oueis, H. Li, J. Wang, W. Wang, Org. Lett. 2008, 10, 1923. 10.1021/ol800417q CASPubMedWeb of Science®Google Scholar 9For a review on catalysis by α,α-diaryl prolinol ethers, see: Google Scholar 9aC. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042; 10.1002/ange.200602943 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2006, 45, 7876; for selected leading references, see: 10.1002/anie.200602943 CASPubMedWeb of Science®Google Scholar 9bM. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804; 10.1002/ange.200462101 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 794; 10.1002/anie.200462101 CASPubMedWeb of Science®Google Scholar 9cY. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284; 10.1002/ange.200500599 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 4212; 10.1002/anie.200500599 CASPubMedWeb of Science®Google Scholar 9dM. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964; 10.1021/ja051808s CASPubMedWeb of Science®Google Scholar 9eD. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861; 10.1038/nature04820 CASPubMedWeb of Science®Google Scholar 9fW. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354; 10.1021/ja063328m CASPubMedWeb of Science®Google Scholar 9gA. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119; 10.1002/ange.200604479 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 1101; 10.1002/anie.200604479 CASPubMedWeb of Science®Google Scholar 9hY. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 5608; 10.1021/ja800345r CASPubMedWeb of Science®Google Scholar 9iP. García-García, A. Ladépêche, R. Halder, B. List, Angew. Chem. 2008, 120, 4797; 10.1002/ange.200800847 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4719; 10.1002/anie.200800847 CASPubMedWeb of Science®Google Scholar 9jY. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800; 10.1002/ange.200801130 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4722. 10.1002/anie.200801130 CASPubMedWeb of Science®Google Scholar 10For our previous studies on asymmetric aminocatalysis, see: Google Scholar 10aJ.-W. Xie, L. Yue, D. Xue, X.-L. Ma, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Chem. Commun. 2006, 1563; 10.1039/b600647g CASPubMedWeb of Science®Google Scholar 10bW. Chen, X.-H. Yuan, R. Li, W. Du, Y. Wu, L.-S. Ding, Y.-C. Chen, Adv. Synth. Catal. 2006, 348, 1818; 10.1002/adsc.200606102 CASWeb of Science®Google Scholar 10cJ.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393; 10.1002/ange.200603612 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 389; 10.1002/anie.200603612 CASPubMedWeb of Science®Google Scholar 10dW. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811; 10.1002/ange.200702618 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 7667; 10.1002/anie.200702618 CASPubMedWeb of Science®Google Scholar 10eT.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, Z.-Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671. 10.1021/ol701648x CASPubMedWeb of Science®Google Scholar 11For a discussion on the effects of water in aminocatalysis, see: Google Scholar 11aY. Hayashi, Angew. Chem. 2006, 118, 8281; 10.1002/ange.200603378 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 8103; 10.1002/anie.200603378 CASPubMedWeb of Science®Google Scholar 11bA. P. Brogan, T. J. Dickerson, K. D. Janda, Angew. Chem. 2006, 118, 8278; 10.1002/ange.200601392 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 8100; 10.1002/anie.200601392 CASPubMedWeb of Science®Google Scholar 11cD. G. Blackmond, A. Armstrong, V. Coombe, A. Wells, Angew. Chem. 2007, 119, 3872; 10.1002/ange.200604952 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 3798. 10.1002/anie.200604952 CASPubMedWeb of Science®Google Scholar 12CCDC 701465 (4 l) and 701466 (6) contain the supplemetary 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. Google Scholar 13For recent applications of acetaldehyde in enamine catalysis, see: Google Scholar 13aY. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 2112; 10.1002/ange.200704870 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 2082; 10.1002/anie.200704870 CASPubMedWeb of Science®Google Scholar 13bJ. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature 2008, 452, 453; 10.1038/nature06740 CASPubMedWeb of Science®Google Scholar 13csee references [9i] and [9j]; Google Scholar 13dfor a Highlight, see: B. Alcaide, P. Almendros, Angew. Chem. 2008, 120, 4710; 10.1002/ange.200801231 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4632. 10.1002/anie.200801231 CASPubMedWeb of Science®Google Scholar 14For additions to vinyl ketones, see: Google Scholar 14aP. Melchiorre, K. A. Jørgensen, J. Org. Chem. 2003, 68, 4151; 10.1021/jo026837p CASPubMedWeb of Science®Google Scholar 14bT. J. Peelen, Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 11598; 10.1021/ja0532584 CASPubMedWeb of Science®Google Scholar 14cY. Chi, S. H. Gellman, Org. Lett. 2005, 7, 4253; 10.1021/ol0517729 CASPubMedWeb of Science®Google Scholar 14dY. Chi, S. T. Scroggins, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 6322; for additions to quinones, see: 10.1021/ja8013456 CASPubMedWeb of Science®Google Scholar 14eJ. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2007, 119, 5616; 10.1002/ange.200701207 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 5520; for intramolecular Michael addition to enones, see: 10.1002/anie.200701207 CASPubMedWeb of Science®Google Scholar 14fM. T. Hechavarria Fonseca, B. List, Angew. Chem. 2004, 116, 4048; 10.1002/ange.200460578 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 3958; 10.1002/anie.200460578 CASPubMedWeb of Science®Google Scholar 14gJ. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036; 10.1021/ja055735o CASPubMedWeb of Science®Google Scholar 14hY. Hayashi, H. Gotoh, T. Tamura, H. Yamaguchi, R. Masui, M. Shoji, J. Am. Chem. Soc. 2005, 127, 16028; 10.1021/ja055740s CASPubMedWeb of Science®Google Scholar 14iN. T. Vo, R. D. M. Pace, F. O'Hara, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 404. 10.1021/ja077457u CASPubMedWeb of Science®Google Scholar 15As suggested by Juhl and Jørgensen for a related system,[8a] the catalyst may induce the ketimine to approach the aldehyde in an endo-selective manner to afford the observed chiral hemiaminal 4. However, at present a formal Michael addition followed by a ring-closure process cannot be ruled out (see reference [8c]). Google Scholar Citing Literature Volume120, Issue51December 8, 2008Pages 10119-10122 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. ReferencesRelatedInformation