Fe-Catalyzed Thioesterification of Carboxylic Esters
Dipl.-Chem. Silja Magens
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285
Search for more papers by this authorCorresponding Author
Prof. Dr. Bernd Plietker
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285Search for more papers by this authorDipl.-Chem. Silja Magens
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285
Search for more papers by this authorCorresponding Author
Prof. Dr. Bernd Plietker
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 711-68564285Search for more papers by this authorGraphical Abstract
Second nature: Starting from shelf-stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical-ligation-type peptide formation, which suggests that the thiol may act as a co-catalyst for future 1,2-additions of pronucleophiles to carboxylic esters.
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 |
|---|---|
| chem_201101073_sm_miscellaneous_information.pdf1.1 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
- 1J. M. Berg, J. L. Tymoczko, L. Stryer, Biochemistry, 6th ed., W. H. Freeman, New York, 2006.
- 2
- 2aP. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science 1994, 266, 776–779;
- 2bP. E. Dawson, S. B. Kent, Annu. Rev. Biochem. 2000, 69, 923–960;
- 2cD. Macmillan, Angew. Chem. 2006, 118, 7830–7834;
10.1002/ange.200602945 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 7668–7672;
- 2dC. F. W. Becker in Chemical Biology (Eds.: ), Wiley-VCH, Weinheim, 2009, pp. 145–157.
- 3
- 3aM. Q. Xu, F. B. Perler, EMBO J. 1996, 15, 5146–5153;
- 3bC. J. Noren, J. Wang, F. B. Perler, Angew. Chem. 2000, 112, 458–476;
10.1002/(SICI)1521-3757(20000204)112:3<458::AID-ANGE458>3.0.CO;2-7 Google ScholarAngew. Chem. Int. Ed. 2000, 39, 450–466.10.1002/(SICI)1521-3773(20000204)39:3<450::AID-ANIE450>3.0.CO;2-F CASPubMedWeb of Science®Google Scholar
- 4
- 4aN. Iranpoor, H. Firouzabadi, D. Khalili, S. Motevalli, J. Org. Chem. 2008, 73, 4882–4887;
- 4bH. Tokuyama, S. Yokoshima, S.-C. Lin, L. Li, T. Fukuyama, Synthesis 2002, 1121–1123;
- 4cB. Neises, W. Steglich, Angew. Chem. 1978, 90, 556–557; Angew. Chem. Int. Ed. Engl. 1978, 17, 522–523;
- 4dM. Pittelkow, F. S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen, Synthesis 2004, 2485–2492;
- 4eK. Ishihara, M. Nakayama, S. Ohara, H. Yamamoto, Tetrahedron 2002, 58, 8179–8188.
- 5
- 5aR. P. Hatch, S. M. Weinreb, J. Org. Chem. 1977, 42, 3960–3961;
- 5bH. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn. 1991, 64, 111–117;
- 5cP. Tecilla, V. Jubian, A. D. Hamilton, Tetrahedron 1995, 51, 435–448;
- 5dD. E. Ponde, V. H. Deshpande, V. J. Bulbule, A. Sudalai, A. S. Gajare, J. Org. Chem. 1998, 63, 1058–1063;
- 5eR. H. Tale, A. D. Sagar, H. D. Adude, Synlett 2006, 0415–0418.
- 6A base-promoted thermal transthioesterification of aryl carboxylic acid esters was recently reported: D. A. Watson, X. Fan, S. L. Buchwald, J. Org. Chem. 2008, 73, 7096–7101.
- 7
- 7aW. Yang, D. G. Drueckhammer, J. Am. Chem. Soc. 2001, 123, 11004–11009;
- 7bW. Yang, D. G. Drueckhammer, Org. Lett. 2000, 2, 4133–4136;
- 7cE. A. Castro, Chem. Rev. 1999, 99, 3505–3524;
- 7dD. W. Deerfield II, L. G. Pedersen, J. Mol. Struct.: THEOCHEM 1995, 358, 99–106;
- 7eD. R. Marshall, P. J. Thomas, C. J. M. Stirling, J. Chem. Soc. Perkin Trans. 2 1977, 1898–1909;
- 7fK. T. Douglas, N. F. Yaggi, J. Chem. Soc. Perkin Trans. 2 1980, 1037–1044;
- 7gJ. P. Idoux, P. T. R. Hwang, C. K. Hancock, J. Org. Chem. 1973, 38, 4239–4243;
- 7hW. P. Jencks, M. Gilchrist, J. Am. Chem. Soc. 1964, 86, 4651–4654;
- 7iD. K. A. Connors, M. L. Bender, J. Org. Chem. 1961, 26, 2498–2504.
- 8
- 8aS. Magens, M. Ertelt, A. Jatsch, B. Plietker, Org. Lett. 2008, 10, 53–56;
- 8bS. Magens, B. Plietker, J. Org. Chem. 2010, 75, 3715–3721.
Citing Literature
