Mild Metal‐Free Tandem α‐Alkylation/Cyclization of N‐Benzyl Carbamates with Simple Olefins
Identifieur interne : 000448 ( Main/Merge ); précédent : 000447; suivant : 000449Mild Metal‐Free Tandem α‐Alkylation/Cyclization of N‐Benzyl Carbamates with Simple Olefins
Auteurs : Heinrich Richter [Allemagne] ; Roland Fröhlich [Allemagne] ; Constantin-Gabriel Daniliuc [Allemagne] ; Olga García Anche O [Allemagne]Source :
- Angewandte Chemie International Edition [ 1433-7851 ] ; 2012-08-20.
English descriptors
- Entity :
- org : DFG, Deutsche Forschungsgemeinschaft, Fonds, Hoffmann-La Roche Inc., US Patent Appl.
- pers : A. A. Deshmukh, A. Alanine, A. Blasko, A. Bourson, A. Cherkasov, A. Fokin, A. G. Yurchenko, A. Grossi, A. I. Yaroshinsky, A. Nagaki, A. Nardi, A. Studer, B. Buettelmann, B. E. Maryanoff, B. Gan, B. M. Trost, C. A. Maryanoff, C. Brückner, C. E. Hoesl, C. Feau, C. Liu, C. M. Tice, C. Parsons, C. S. Yeung, Constantin-Gabriel Daniliuc, D. A. Claremon, D. Lednicer, D. Sureshkumar, D. W. Ovenall, E. LeBlanc, E. Pinard, E. Yoshida, F. Foubelo, F. H. Foersterling, F. Kakiuchi, F. Maspero, F. Q. Han, G. D. Mateescu, G. Daniliuc, G. Fischer, G. Hçfner, G. K. S. Prakash, G. Liang, G. Quack, G. Sipos, G. Trube, H. Beer, H. C. Zhang, H. E. Zaugg, H. Hiemstra, H. K. Erichsen, H. Li, H. Liu, H. Richter, H. Zhang, I. Fleming, I. J. Turchi, I. Praschak, J. Alem, J. G. Shih, J. H. Cohen, J. Li, J. M. Bobbitt, J. Med, J. Org, J. Polym, J. S. Fossey, J. S. Ulicki, J. Shi, J. Sun, J. Wang, J. Yoshida, K. C. Hultzsch, K. Endo, K. H. Chan, K. L. Troelsen, K. Leftheris, K. Nakamura, K. R. Campos, K. T. Wanner, L. A. Mitscher, L. B. Barbier, L. Cao, L. Tebben, L. Zhuang, M. G. Clerici, M. J. Moolenaar, M. K. Gurjar, M. Klussmann, M. M. Hossain, M. Tada, M. Yus, N. A. Lack, N. Chatani, N. Merbouh, N. Uddin, N.H. Lin, O. G. MancheÇo, O. García, O. Schnieder, Olga García, P. A. Gunchenko, P. A. Krasutsky, P. Axerio-Cilies, P. Deng, P. Heitz, P. Jiang, P. P. Pradhan, P. S. Rennie, P. Tavassoli, P. W. Roesky, Peter Nesvadba, R. Frçhlich, R. K. Guy, R. Rohlmann, R. Schleyer, R. Wyler, Recent, Roland Frçhlich, S. B. Singh, S. J. Holmes, S. Murai, S. Pan, S. R. Mehta, S. Roever, S. S. Deshmukh, S. Suga, S. Yorimitsu, T. Asaumi, T. E. Müller, T. Endo, T. Ikeda, T. M. Gund, T. R. Farrell, T. Shibata, T. Takata, To, V. Buss, V. M. Dong, V. Mutel, V. V. Krishnamurthy, W. A. Nugent, W. Bailey, W. N. Speckamp, W. Shi, X. Cai, X. Song, Y. Tsutsui, Y. Wang, Y. Ye, Z. Xu.
- place : Besendorf, Cambridge, Denmark, York.
- Teeft :
- Acyclic benzyl carbamate, Angew, Angewandte communication, Appl, Carbamate, Chem, Complex mixture, Derivative, Equiv, Initial study, Lett, Lewis acid, Major isomer, Metal catalyst, More likely, Nitrogen atom, Nitrogen compound, Nitrogen group, Nonactivated olefin, Olefin, Other hand, Oxazinones, Patent appl, Recent review, Relative configuration, Room temperature, Simple olefin, Suitable substrate, Tempo salt, Tetrahedron lett, Verlag gmbh, Weinheim angew.
Abstract
Easy does it! The chemoselective oxidative α‐C(sp3)H alkylation/cyclization reaction of N‐benzyl carbamates using simple mono‐, di‐, and trisubstituted olefins provides functionalized N‐heterocycles such as oxazinones (see picture). A TEMPO oxoammonium salt serves as the oxidant, making it possible to carry out the reaction at low temperatures. Neither a metal catalyst nor preactivation in the α‐position to the nitrogen group are needed.
Url:
DOI: 10.1002/anie.201202379
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ISTEX:63D81E80774264194570BE38205FD859E3B8B404Le document en format XML
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<term>S. Yorimitsu</term>
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<term>T. Takata</term>
<term>To</term>
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<keywords scheme="Teeft" xml:lang="en"><term>Acyclic benzyl carbamate</term>
<term>Angew</term>
<term>Angewandte communication</term>
<term>Appl</term>
<term>Carbamate</term>
<term>Chem</term>
<term>Complex mixture</term>
<term>Derivative</term>
<term>Equiv</term>
<term>Initial study</term>
<term>Lett</term>
<term>Lewis acid</term>
<term>Major isomer</term>
<term>Metal catalyst</term>
<term>More likely</term>
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<term>Nitrogen compound</term>
<term>Nitrogen group</term>
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<term>Olefin</term>
<term>Other hand</term>
<term>Oxazinones</term>
<term>Patent appl</term>
<term>Recent review</term>
<term>Relative configuration</term>
<term>Room temperature</term>
<term>Simple olefin</term>
<term>Suitable substrate</term>
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<front><div type="abstract" xml:lang="en">Easy does it! The chemoselective oxidative α‐C(sp3)H alkylation/cyclization reaction of N‐benzyl carbamates using simple mono‐, di‐, and trisubstituted olefins provides functionalized N‐heterocycles such as oxazinones (see picture). A TEMPO oxoammonium salt serves as the oxidant, making it possible to carry out the reaction at low temperatures. Neither a metal catalyst nor preactivation in the α‐position to the nitrogen group are needed.</div>
</front>
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