Artigo Revisado por pares

Highly Stereoselective Cyclopropanation of α,β‐Unsaturated Carbonyl Compounds with Methyl (Diazoacetoxy)acetate Catalyzed by a Chiral Ruthenium(II) Complex

2013; Wiley; Volume: 125; Issue: 22 Linguagem: Inglês

10.1002/ange.201300468

ISSN

1521-3757

Autores

Soda Chanthamath, Suguru Takaki, Kazutaka Shibatomi, Seiji Iwasa,

Tópico(s)

Asymmetric Hydrogenation and Catalysis

Resumo

Angewandte ChemieVolume 125, Issue 22 p. 5930-5933 Zuschrift Highly Stereoselective Cyclopropanation of α,β-Unsaturated Carbonyl Compounds with Methyl (Diazoacetoxy)acetate Catalyzed by a Chiral Ruthenium(II) Complex† Soda Chanthamath, Soda Chanthamath Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorSuguru Takaki, Suguru Takaki Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorProf. Dr. Kazutaka Shibatomi, Prof. Dr. Kazutaka Shibatomi Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorProf. Dr. Seiji Iwasa, Corresponding Author Prof. Dr. Seiji Iwasa [email protected] Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this author Soda Chanthamath, Soda Chanthamath Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorSuguru Takaki, Suguru Takaki Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorProf. Dr. Kazutaka Shibatomi, Prof. Dr. Kazutaka Shibatomi Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this authorProf. Dr. Seiji Iwasa, Corresponding Author Prof. Dr. Seiji Iwasa [email protected] Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580 (Japan)Search for more papers by this author First published: 16 April 2013 https://doi.org/10.1002/ange.201300468Citations: 10 † This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 20550137) from the Japan Society for the Promotion of Science. Read 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 Spannende Dreiecke: Die Titelreaktion liefert Bicarbonylcyclopropane, aus denen mit hohen Ausbeuten und Stereoselektivitäten nützliche Intermediate zugänglich sind. Das System wurde außerdem für die enantioselektive Totalsynthese von Spirocyclopropanoxindol genutzt, einem nichtnucleosiden Inhibitor der reversen Transcriptase von HIV-1. 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_201300468_sm_miscellaneous_information.pdf24.1 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 1aW. A. Donaldson, Tetrahedron 2001, 57, 8589–8627; 10.1016/S0040-4020(01)00777-3 CASWeb of Science®Google Scholar 1bJ. Pietruszka, Chem. Rev. 2003, 103, 1051–1070; 10.1021/cr010027g CASPubMedWeb of Science®Google Scholar 1cL. A. Wessjohann, W. Brandt, T. Thiemann, Chem. Rev. 2003, 103, 1625–1647; 10.1021/cr0100188 CASPubMedWeb of Science®Google Scholar 1dH. Lebel, J.-F. Marcoux, C. Molinaro, A. B. J. Charette, Chem. Rev. 2003, 103, 977–1050; 10.1021/cr010007e CASPubMedWeb of Science®Google Scholar 1eA. Armstrong, J. N. Scutt, Chem. Commun. 2004, 510–511; 10.1039/B316142K CASPubMedWeb of Science®Google Scholar 1fH. Pellissier, Tetrahedron 2008, 64, 7041–7095; 10.1016/j.tet.2008.04.079 CASWeb of Science®Google Scholar 1gD. Y.-K. Chen, R. H. Pouwer, J.-A. Richard, Chem. Soc. Rev. 2012, 41, 4631–4642. 10.1039/c2cs35067j CASPubMedWeb of Science®Google Scholar 2 2aM. P. Doyle, B. D. Brandes, A. P. Kazala, R. J. Pieters, M. B. Jarstfer, L. M. Watkins, C. T. Eagle, Tetrahedron Lett. 1990, 31, 6613–6616; 10.1016/S0040-4039(00)97128-4 CASWeb of Science®Google Scholar 2bR. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005–6008; 10.1016/S0040-4039(00)98014-6 CASWeb of Science®Google Scholar 2cD. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726–728; 10.1021/ja00002a080 CASWeb of Science®Google Scholar 2dH. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223–2224; 10.1021/ja00084a104 CASWeb of Science®Google Scholar 2eJ. A. Miller, W. Jin, S. T. Nguyen, Angew. Chem. 2002, 114, 3077–3080; 10.1002/1521-3757(20020816)114:16 3.0.CO;2-O Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2953–2956; 10.1002/1521-3773(20020816)41:16 3.0.CO;2-2 CASPubMedWeb of Science®Google Scholar 2fM. Itagaki, Y. Yamamoto, Tetrahedron Lett. 2006, 47, 523–525; 10.1016/j.tetlet.2005.11.086 CASWeb of Science®Google Scholar 2gV. D. M. Hoang, P. A. N. Reddy, T.-J. Kim, Tetrahedron Lett. 2007, 48, 8014–8017; 10.1016/j.tetlet.2007.09.035 CASWeb of Science®Google Scholar 2hY. Chen, X. P. Zhang, J. Org. Chem. 2007, 72, 5931–5934; 10.1021/jo070997p CASPubMedWeb of Science®Google Scholar 2iH. Suematsu, S. Kanchiku, T. Uchida, T. Katsuki, J. Am. Chem. Soc. 2008, 130, 10327–10337. 10.1021/ja802561t CASPubMedWeb of Science®Google Scholar 3For selected examples of Cu-catalyzed asymmetric cyclopropanation, see: Google Scholar 3aW. Kirmse, Angew. Chem. 2003, 115, 1120–1125; 10.1002/ange.200390261 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 1088–1093; 10.1002/anie.200390290 PubMedWeb of Science®Google Scholar 3bH. A. McManus, P. J. Guiry, Chem. Rev. 2004, 104, 4151–4202; 10.1021/cr040642v CASPubMedWeb of Science®Google Scholar 3cT. Portada, M. Roje, Z. Hamersak, M. Zinic, Tetrahedron Lett. 2005, 46, 5957–5959; 10.1016/j.tetlet.2005.06.155 CASWeb of Science®Google Scholar 3dG. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561–3651; 10.1021/cr0505324 CASPubMedWeb of Science®Google Scholar 3eT. Portada, M. Roje, Z. Raza, V. Čaplar, M. Žinić, V. Šunjić, Eur. J. Org. Chem. 2007, 838–856. 10.1002/ejoc.200600827 CASWeb of Science®Google Scholar 4For selected examples of Rh-catalyzed asymmetric cyclopropanation, see: Google Scholar 4aM. P. Doyle, M. Yan, H.-M. Gau, E. C. Blossey, Org. Lett. 2003, 5, 561–563; 10.1021/ol027475a CASPubMedWeb of Science®Google Scholar 4bY. Lou, M. Horikawa, R. A. Kloster, N. A. Hawryluk, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 8916–8918; 10.1021/ja047064k CASPubMedWeb of Science®Google Scholar 4cP. Müller, G. Bernardinelli, Y. F. Allenbach, M. Ferri, S. Grass, Synlett 2005, 1397–1400; 10.1055/s-2005-868501 CASWeb of Science®Google Scholar 4dH. M. L. Davies, A. M. Walji, Org. Lett. 2005, 7, 2941–2944; 10.1021/ol0508835 CASPubMedWeb of Science®Google Scholar 4eP. Müller, G. Bernardinelli, Y. F. Allenbach, S. Chappellet, A. Ghanem, Synthesis 2006, 1689–1696. 10.1055/s-2006-926452 CASWeb of Science®Google Scholar 5For selected examples of Ru-catalyzed asymmetric cyclopropanation, see: Google Scholar 5aA. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746–4756; 10.1002/chem.200305045 CASPubMedWeb of Science®Google Scholar 5bS. Iwasa, S. Tsushima, K. Nishiyama, Y. Tsuchiya, F. Takezawa, H. Nishiyama, Tetrahedron: Asymmetry 2003, 14, 855–865; 10.1016/S0957-4166(03)00168-X CASWeb of Science®Google Scholar 5cA. B. Charette, J.-E. Bouchard, Can. J. Chem. 2005, 83, 533–542; 10.1139/v05-074 CASWeb of Science®Google Scholar 5dJ. A. Miller, B. A. Gross, M. A. Zhuravel, W. Jin, S. T. Nguyen, Angew. Chem. 2005, 117, 3953–3957; 10.1002/ange.200460887 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 3885–3889; 10.1002/anie.200460887 CASPubMedWeb of Science®Google Scholar 5eC. Bonaccorsi, F. Santoro, S. Gischig, A. Mezzetti, Organometallics 2006, 25, 2002–2010. 10.1021/om0510627 CASWeb of Science®Google Scholar 6For selected examples of Co-catalyzed asymmetric cyclopropanation, see: Google Scholar 6aL. Huang, Y. Chen, G.-Y. Gao, X. P. Zhang, J. Org. Chem. 2003, 68, 8179–8184; 10.1021/jo035088o CASPubMedWeb of Science®Google Scholar 6bY. Chen, K. B. Fields, X. P. Zhang, J. Am. Chem. Soc. 2004, 126, 14718–14719; 10.1021/ja044889l CASPubMedWeb of Science®Google Scholar 6cJ. Gao, F. R. Woolley, R. A. Zingaro, Org. Biomol. Chem. 2005, 3, 2126–2128; 10.1039/b503971a CASPubMedWeb of Science®Google Scholar 6dT. Uchida, T. Katsuki, Synthesis 2006, 1715–1723; CASWeb of Science®Google Scholar 6eY. Chen, J. V. Ruppel, X. P. Zhang, J. Am. Chem. Soc. 2007, 129, 12074–12075; 10.1021/ja074613o CASPubMedWeb of Science®Google Scholar 6fJ. V. Ruppel, T. J. Gauthier, N. L. Snyder, J. A. Perman, X. P. Zhang, Org. Lett. 2009, 11, 2273–2276. 10.1021/ol9005882 CASPubMedWeb of Science®Google Scholar 7 7aS. D. Larsen, T. Barf, C. Liljebris, P. D. May, D. Ogg, T. J. O’Sullivan, B. J. Palazuk, H. J. Schostarez, F. C. Stevens, J. E. Bleasdale, J. Med. Chem. 2002, 45, 598–622; 10.1021/jm010393s CASPubMedWeb of Science®Google Scholar 7bB. M. Trost, O. Dirat, J. L. Gunzner, Angew. Chem. 2002, 114, 869–871; 10.1002/1521-3757(20020301)114:5 3.0.CO;2-G Google ScholarAngew. Chem. Int. Ed. 2002, 41, 841–843; 10.1002/1521-3773(20020301)41:5 3.0.CO;2-2 CASPubMedWeb of Science®Google Scholar 7cB. M. Trost, J. L. Gunzner, O. Dirat, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 10396–10415; 10.1021/ja0205232 CASPubMedWeb of Science®Google Scholar 7dM.-X. Zhang, P. E. Eaton, Angew. Chem. 2002, 114, 2273–2275; 10.1002/1521-3757(20020617)114:12 3.0.CO;2-8 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2169–2171; 10.1002/1521-3773(20020617)41:12 3.0.CO;2-H CASPubMedWeb of Science®Google Scholar 7eJ. A. Miller, E. J. Hennessy, W. J. Marshall, M. A. Scialdone, S. T. Nguyen, J. Org. Chem. 2003, 68, 7884–7886; 10.1021/jo0344079 CASPubMedWeb of Science®Google Scholar 7fU. S. Sørensen, T. J. Bleisch, A. E. Kingston, R. A. Wright, B. G. Johnson, D. D. Schoepp, P. L. Ornstein, Bioorg. Med. Chem. 2003, 11, 197–205; 10.1016/S0968-0896(02)00387-5 CASPubMedWeb of Science®Google Scholar 7gJ. K. Pokorski, M. C. Myers, D. H. Appella, Tetrahedron Lett. 2005, 46, 915–917; 10.1016/j.tetlet.2004.12.061 CASWeb of Science®Google Scholar 7hK. Kagayama, T. Morimoto, S. Nagata, F. Katoh, X. Zhang, N. Inoue, A. Hashino, K. Kageyama, J. Shikaura, T. Niwa, Bioorg. Med. Chem. 2009, 17, 6959–6970. 10.1016/j.bmc.2009.08.014 CASPubMedWeb of Science®Google Scholar 8 8aA.-M. Abu-Elfotoh, K. Phomkeona, K. Shibatomi, S. Iwasa, Angew. Chem. 2010, 122, 8617–8621; 10.1002/ange.201002240 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 8439–8443; 10.1002/anie.201002240 CASPubMedWeb of Science®Google Scholar 8bS. Chanthamath, K. Phomkeona, K. Shibatomi, S. Iwasa, Chem. Commun. 2012, 48, 7750–7752; 10.1039/c2cc32706f CASPubMedWeb of Science®Google Scholar 8cS. Chanthamath, D. T. Nguyen, K. Shibatomi, S. Iwasa, Org. Lett. 2013, 15, 772–775. 10.1021/ol303404c CASPubMedWeb of Science®Google Scholar 9Acetonyl diazoacetate (ADA) is a novel diazo compound that was synthesized by using Fukuyama’s method: (see the Supporting Information). Google Scholar 10K. Hori, H. Kazuno, K. Nomura, E. Yoshii, Tetrahedron Lett. 1993, 34, 2183–2186. 10.1016/S0040-4039(00)60377-5 CASWeb of Science®Google Scholar 11T. Goto, K. Takeda, M. Anada, K. Ando, S. Hashimoto, Tetrahedron Lett. 2011, 52, 4200–4203. 10.1016/j.tetlet.2011.06.008 CASWeb of Science®Google Scholar 12 12aA. B. Charette, H. Lebel, J. Am. Chem. Soc. 1996, 118, 10327–10328; for the determination of the absolute configuration of 1,2-cyclopropane dimethanol, see: 10.1021/ja9619420 CASWeb of Science®Google Scholar 12bA. G. M. Barrett, D. Hamprecht, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 8608–8615; 10.1021/ja9708326 CASWeb of Science®Google Scholar 12cW. S. McDonald, C. A. Verbicky, C. K. Zercher, J. Org. Chem. 1997, 62, 1215–1222. 10.1021/jo961136b CASWeb of Science®Google Scholar 13For the determination of the absolute configuration of 1,2-cyclopropane dicarboxylic acid, see: M. P. Singh, B. Plouvier, G. C. Hill, J. Gueck, R. T. Pon, J. W. Lown, J. Am. Chem. Soc. 1994, 116, 7006–7020. 10.1021/ja00095a002 CASWeb of Science®Google Scholar 14T. Jiang, K. L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Y.-H. Wu, Y. He, Bioorg. Med. Chem. Lett. 2006, 16, 2105–2108. 10.1016/j.bmcl.2006.01.073 CASPubMedWeb of Science®Google Scholar Citing Literature Volume125, Issue22May 27, 2013Pages 5930-5933 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

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