Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide†
Dr. Karin Weidner
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorZhongdong Sun
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorCorresponding Author
Dr. Naoya Kumagai
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)Search for more papers by this authorCorresponding Author
Prof. Dr. Masakatsu Shibasaki
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)Search for more papers by this authorDr. Karin Weidner
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorZhongdong Sun
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorCorresponding Author
Dr. Naoya Kumagai
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)Search for more papers by this authorCorresponding Author
Prof. Dr. Masakatsu Shibasaki
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)Search for more papers by this authorThis work was financially supported by JST, ACT-C, and KAKENHI (25713002) from JSPS. Dr. Ryuichi Sawa and Yumiko Kubota are gratefully acknowledged for 15N NMR analysis. We thank Dr. Tomoyuki Kimura for assistance with X-ray crystallography. Dr. Fernando A. Arteaga is acknowledged for studies on aliphatic aldehydes.
Abstract
A direct aldol reaction of an α-azido 7-azaindolinylamide, promoted by a Cu-based cooperative catalyst, is documented. Aromatic aldehydes bearing an ortho substituent exhibited diastereodivergency depending on the nature of the chiral ligands used. Smooth reactions with ynals highlighted the broad substrate scope. A vicinal azido alcohol unit in the product allowed direct access to the corresponding aziridine and facile hydrolysis of the 7-azaindolinylamide moiety furnished enantioenriched β-hydroxy-α-azido carboxylic acid derivatives.
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_201501607_sm_miscellaneous_information.pdf26.3 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
- 1aT. Ooi, K. Maruoka, J. Synth. Org. Chem. Jpn. 2003, 61, 43;
- 1bK. Makino, Y. Hamada, J. Synth. Org. Chem. Jpn. 2005, 63, 1198;
- 1cY.-C. Luo, H.-H. Zhang, Y. Wang, P.-F. Zu, Acc. Chem. Res. 2010, 43, 1317;
- 1dY. Zhang, H. Farrants, X. Li, Chem. Asian J. 2014, 9, 1752.
- 2Reviews of glycopeptide antibiotics:
- 2aK. C. Nicolaou, C. N. Boddy, S. Bräse, N. Winssinger, Angew. Chem. Int. Ed. 1999, 38, 2096;
10.1002/(SICI)1521-3773(19990802)38:15<2096::AID-ANIE2096>3.0.CO;2-F CAS PubMed Web of Science® Google ScholarAngew. Chem. 1999, 111, 2230;10.1002/(SICI)1521-3757(19990802)111:15<2230::AID-ANGE2230>3.0.CO;2-V Web of Science® Google Scholar
- 2bD. H. Williams, B. Bardsley, Angew. Chem. Int. Ed. 1999, 38, 1172;
10.1002/(SICI)1521-3773(19990503)38:9<1172::AID-ANIE1172>3.0.CO;2-C PubMed Web of Science® Google ScholarAngew. Chem. 1999, 111, 1264;
- 2cD. L. Boger, Med. Res. Rev. 2001, 21, 356.
- 3Review of an enzymatic approach using modified threonine aldolases: N. Dückers, K. Baer, S. Simon, H. Gröger, W. Hummel, Appl. Microbiol. Biotechnol. 2010, 88, 409.
- 4Review: M. J. O’Donnell, Acc. Chem. Res. 2004, 37, 506.
- 5C. M. Gasparski, M. J. Miller, Tetrahedron 1991, 47, 5367.
- 6
- 6aS. Mettath, G. S. C. Srikanth, B. S. Dangerfield, S. L. Castle, J. Org. Chem. 2004, 69, 6489;
- 6bB. Ma, J. L. Parkinson, S. L. Castle, Tetrahedron Lett. 2007, 48, 2083.
- 7
- 7aT. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 4542;
10.1002/1521-3773(20021202)41:23<4542::AID-ANIE4542>3.0.CO;2-3 CAS PubMed Web of Science® Google ScholarAngew. Chem. 2002, 114, 4724;
- 7bT. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 9685;
- 7cT. Kano, Q. Lan, X. Wang, K. Maruoka, Adv. Synth. Catal. 2007, 349, 556;
- 7dM. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, Chem. Asian J. 2008, 3, 1702.
- 8A partially successful example (moderate ee), using a LaLi3 heterobimetallic catalyst: N. Yoshikawa, M. Shibasaki, Tetrahedron 2002, 58, 8289.
- 9B. M. Trost, F. Miege, J. Am. Chem. Soc. 2014, 136, 3016.
- 10Mukaiyama aldol reactions using ketene silyl acetals derived from glycinate Schiff bases:
- 10aM. Horikawa, J. Busch-Petersen, E. J. Corey, Tetrahedron Lett. 1999, 40, 3843;
- 10bJ. Kobayashi, M. Nakamura, Y. Mori, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 9192.
- 11Review: A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, V. G. Nenajdenko, Chem. Rev. 2010, 110, 5235.
- 12
- 12aY. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405;
- 12bF. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133, 1710.
- 13
- 13aM.-X. Xue, C. Guo, L.-Z. Gong, Synlett 2009, 2191;
- 13bT. Yoshino, H. Morimoto, G. Lu, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 17082.
- 14
- 14aH. Suga, K. Ikai, T. Ibata, J. Org. Chem. 1999, 64, 7040;
- 14bD. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. Int. Ed. 2001, 40, 1884;
10.1002/1521-3773(20010518)40:10<1884::AID-ANIE1884>3.0.CO;2-9 CAS PubMed Web of Science® Google ScholarAngew. Chem. 2001, 113, 1936;
- 14cX. Chen, Y. Zhu, Z. Qiao, M. Xie, L. Lin, X. Liu, X. Feng, Chem. Eur. J. 2010, 16, 10124.
- 15Other indirect approaches to β-hydroxy-α-amino esters which require reduction or oxidation of the products. Use of α-nitro esters:
- 15aS. Shirakawa, K. Ota, S. J. Terao, K. Maruoka, Org. Biomol. Chem. 2012, 10, 5753;
- 15bC.-B. Ji, Y.-L. Liu, Z.-Y. Cao, Y.-Y. Zhang, J. Zhou, Tetrahedron Lett. 2011, 52, 6118; use of α-N-phthaloylacetaldehyde:
- 15cR. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 3541.
- 16
- 16aK. Weidner, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2014, 53, 6150; Angew. Chem. 2014, 126, 6264;
- 16bL. Yin, L. Brewitz, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2014, 136, 17958.
- 17Recent reviews on utility of organic azides:
- 17aS. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. Int. Ed. 2005, 44, 5188; Angew. Chem. 2005, 117, 5320;
- 17b Organic Azides: Syntheses and Applications (Eds.: ), Wiley, Chichester, UK, 2010.
- 18Reviews of direct aldol reaction:
- 18aB. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595;
- 18bW. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580;
- 18cS. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471;
- 18dB. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600.
- 19Comprehensive review of α-azido ketones: T. Patonay, K. Kónya, É. Juhász-Tóth, Chem. Soc. Rev. 2011, 40, 2797.
- 20Chiral auxiliary approach using (R)-3-(2-azidoacetyl)-4-phenyl-thiazolidin-2-thione as an aldol donor with a stoichiometric amount of TiCl4/iPr2NEt: J. Patel, G. Clavé, P. Renard, X. Franck, Angew. Chem. Int. Ed. 2008, 47, 4224; Angew. Chem. 2008, 120, 4292.
- 21Á. Martínez-Castañeda, K. Kedziora, I. Lavandera, H. Rodríguez-Solla, C. Concellón, V. del Amo, Chem. Commun. 2014, 50, 2598.
- 22Recent reviews of cooperative catalysis. Lewis acid/Brønsted base:
- 22aM. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
- 22bN. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2011, 50, 4760; Angew. Chem. 2011, 123, 4856; Lewis acid/Lewis base:
- 22cM. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491;
- 22dD. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655; Lewis acid/Brønsted acid and Lewis acid/Lewis acid;
- 22eH. Yamamoto, K. Futatsugi, Angew. Chem. Int. Ed. 2005, 44, 1924; Angew. Chem. 2005, 117, 1958;
- 22fH. Yamamoto, K. Futatsugi in Acid Catalysis in Modern Organic Synthesis (Eds.: ), Wiley-VCH, Weinheim, 2008.
- 23
- 23aM. Iwata, R. Yazaki, Y. Suzuki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 18244;
- 23bM. Iwata, R. Yazaki, I.-H. Chen, D. Sureshkumar, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2011, 133, 5554.
- 24Although (R)-xyl-Segphos gave better d.r. values, (R)-xyl-BINAP showed broad generality (Table 2).
- 25For further discussions, see the Supporting Information.
- 26Aldehydes bearing electron-donating substituents exhibited low reactivity.
- 27Even after extensive studies on aliphatic aldehydes, only less satisfactory results were obtained. See the Supporting Information.
- 28 Modern Acetylene Chemistry (Eds.: ), Wiley-VCH, Weinheim, 2015.
- 29π-Coordination of a triple bond could be involved to exhibit anti-diastereoselectivity.
- 30Y. Ittah, Y. Sasson, I. Shahak, S. Tsaroom, J. Blum, J. Org. Chem. 1978, 43, 4271.
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.
