Asymmetric organocatalytic Michael addition of azlactones to cis-1,2-bis(phenylsulfonyl)ethene. A simple entry to quaternary α-amino acids
作者： Natalia Bravo , Andrea-Nekane R. Alba , Guillem Valero , Xavier Companyó , Albert Moyano
DOI: 10.1039/C0NJ00321B
关键词:
摘要: Azlactones react with 1,2-bis(phenylsulfonyl)ethene under catalysis by simple chiral thioureas, affording α,α-disubstituted α-amino acid derivatives in good yields and moderate to enantioselectivities.
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sci-hub.se 参考文章(68)
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
Masahiro Terada, Hiroyasu Tanaka, Keiichi Sorimachi, Enantioselective Direct Aldol-Type Reaction of Azlactone via Protonation of Vinyl Ethers by a Chiral Brønsted Acid Catalyst Journal of the American Chemical Society. ,vol. 131, pp. 3430- 3431 ,(2009) , 10.1021/JA8090643
Benjamin List, Richard A. Lerner, Carlos F. Barbas, Proline-Catalyzed Direct Asymmetric Aldol Reactions Journal of the American Chemical Society. ,vol. 122, pp. 2395- 2396 ,(2000) , 10.1021/JA994280Y
Adrien Quintard, Alexandre Alexakis, Organocatalytic addition on 1,2-bis(sulfone)vinylenes leading to an unprecedented rearrangement. Chemistry: A European Journal. ,vol. 15, pp. 11109- 11113 ,(2009) , 10.1002/CHEM.200901535
M. C. Khosla, K. Stachowiak, R. R. Smeby, F. M. Bumpus, F. Piriou, K. Lintner, S. Fermandjian, Synthesis of [alpha-methyltyrosine-4]angiotensin II: studies of its conformation, pressor activity, and mode of enzymatic degradation. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 78, pp. 757- 760 ,(1981) , 10.1073/PNAS.78.2.757
Sarah Sulzer-Mossé,, Matthieu Tissot, Alexandre Alexakis, First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates. Organic Letters. ,vol. 9, pp. 3749- 3752 ,(2007) , 10.1021/OL7015498
Masanori Kitamura, Seiji Shirakawa, Yuichiro Arimura, Xisheng Wang, Keiji Maruoka, Combinatorial design of simplified high-performance chiral phase-transfer catalysts for practical asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids. Chemistry-an Asian Journal. ,vol. 3, pp. 1702- 1714 ,(2008) , 10.1002/ASIA.200800107
Robert A. Mosey, Jason S. Fisk, Jetze J. Tepe, Stereoselective syntheses of quaternary substituted α-amino acids using oxazol-5-(4H)-ones Tetrahedron-asymmetry. ,vol. 19, pp. 2755- 2762 ,(2008) , 10.1016/J.TETASY.2008.11.033
Andrea-Nekane Balaguer, Xavier Companyó, Teresa Calvet, Mercé Font-Bardía, Albert Moyano, Ramon Rios, Highly Regio‐ and Diastereoselective Oxazol‐5‐one Addition to Nitrostyrenes European Journal of Organic Chemistry. ,vol. 2009, pp. 199- 203 ,(2009) , 10.1002/EJOC.200801005
Tomotaka Okino, Yasutaka Hoashi, Yoshiji Takemoto, Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts Journal of the American Chemical Society. ,vol. 125, pp. 12672- 12673 ,(2003) , 10.1021/JA036972Z