Phosphoric Acid Catalyzed Diastereo- and Enantioselective Synthesis of Substituted 1,3-Diaminotetralins

作者: Guillaume Dagousset , William Erb , Jieping Zhu , Géraldine Masson

DOI: 10.1021/OL500946W

关键词:

摘要: The reaction of anilines and phenylacetaldehydes in the presence chiral phosphoric acid afforded optically active 1,2-trans, 2,3-cis 1,3-diaminotetralins high yields with excellent diastereo- enantioselectivities. trans/cis product was readily isomerized to a trans/trans stereoisomer no significant loss enantiomeric purity.

参考文章(63)
Willard M. Welch, Allen R. Kraska, Reinhard Sarges, B. Kenneth Koe, Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. Journal of Medicinal Chemistry. ,vol. 27, pp. 1508- 1515 ,(1984) , 10.1021/JM00377A021
Béatrice Quiclet-Sire, Guillaume Revol, Samir Z. Zard, Functional primary amines and diamines from alpha-aminoacids. a concise route to substituted 2-aminotetralins. Organic Letters. ,vol. 11, pp. 3554- 3557 ,(2009) , 10.1021/OL901263T
Swati Biswas, Suhong Zhang, Fernando Fernandez, Balaram Ghosh, Juan Zhen, Eldo Kuzhikandathil, Maarten E. A. Reith, Aloke K. Dutta, Further structure-activity relationships study of hybrid 7-{[2-(4-phenylpiperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen-2-ol analogues: identification of a high-affinity D3-preferring agonist with potent in vivo activity with long duration of action. Journal of Medicinal Chemistry. ,vol. 51, pp. 101- 117 ,(2008) , 10.1021/JM070860R
Mark Hadden, Mark Nieuwenhuyzen, Daire Osborne, Paul J. Stevenson, Norris Thompson, Andrew D. Walker, Synthesis of the heterocyclic core of martinelline and martinellic acid Tetrahedron. ,vol. 62, pp. 3977- 3984 ,(2006) , 10.1016/J.TET.2006.02.029
Fei Chen, Tianli Wang, Yanmei He, Ziyuan Ding, Zhiwei Li, Lijin Xu, Qing-Hua Fan, Asymmetric Hydrogenation of N-Alkyl Ketimines with Phosphine-Free, Chiral, Cationic Ru-MsDPEN Catalysts Chemistry - A European Journal. ,vol. 17, pp. 1109- 1113 ,(2011) , 10.1002/CHEM.201002846
Philippe Dupau, Anne-Emmanuelle Hay, Christian Bruneau, Pierre H. Dixneuf, Synthesis of optically active 2-aminotetraline derivatives via enantioselective ruthenium-catalyzed hydrogenation of ene carbamates Tetrahedron-asymmetry. ,vol. 12, pp. 863- 867 ,(2001) , 10.1016/S0957-4166(01)00153-7
Giulia Bergonzini, Lucia Gramigna, Andrea Mazzanti, Mariafrancesca Fochi, Luca Bernardi, Alfredo Ricci, Organocatalytic asymmetric Povarov reactions with 2- and 3-vinylindoles. Chemical Communications. ,vol. 46, pp. 327- 329 ,(2010) , 10.1039/B921113F
Guillaume Dagousset, Fleur Drouet, Géraldine Masson, Jieping Zhu, Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles. Organic Letters. ,vol. 11, pp. 5546- 5549 ,(2009) , 10.1021/OL9023985
Oleg Bondarev, Christian Bruneau, Indirect and direct catalytic asymmetric reductive amination of 2-tetralone Tetrahedron-asymmetry. ,vol. 21, pp. 1350- 1354 ,(2010) , 10.1016/J.TETASY.2010.03.027
Yulong Zhang, Shunxi Dong, Xiaohua Liu, Mingsheng Xie, Yin Zhu, Lili Lin, Xiaoming Feng, Asymmetric Synthesis of cis‐4‐Aminobenzopyran Derivatives Catalyzed by N,N′‐Dioxide–Sc(OTf)3 Complexes Chemistry: A European Journal. ,vol. 17, pp. 13684- 13687 ,(2011) , 10.1002/CHEM.201102058