Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors

作者: Michael Winter , Kirill Faust , Markus Himmelsbach , Mario Waser

DOI: 10.1039/C9OB01134J

关键词:

摘要: The first (3 + 2)-cyclisation of 3,3,3-trifluoropyruvate-derived imines and indandione-based Michael acceptors giving spirocyclic α-CF3-α-proline derivatives was developed.

参考文章(70)
Yongwei Wu, Lin Hu, Zhe Li, Li Deng, Catalytic asymmetric umpolung reactions of imines Nature. ,vol. 523, pp. 445- 450 ,(2015) , 10.1038/NATURE14617
Javier Adrio, Juan C. Carretero, Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides. Chemical Communications. ,vol. 47, pp. 6784- 6794 ,(2011) , 10.1039/C1CC10779H
Xiao-Long Qiu, Feng-Ling Qing, Recent Advances in the Synthesis of Fluorinated Amino Acids European Journal of Organic Chemistry. ,vol. 2011, pp. 3261- 3278 ,(2011) , 10.1002/EJOC.201100032
E. Neil G. Marsh, Fluorinated proteins: From design and synthesis to structure and stability Accounts of Chemical Research. ,vol. 47, pp. 2878- 2886 ,(2014) , 10.1021/AR500125M
Julie Charpentier, Natalja Früh, Antonio Togni, Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents Chemical Reviews. ,vol. 115, pp. 650- 682 ,(2015) , 10.1021/CR500223H
René Smits, Cosimo Damiano Cadicamo, Klaus Burger, Beate Koksch, Synthetic strategies to α-trifluoromethyl and α-difluoromethyl substituted α-amino acids Chemical Society Reviews. ,vol. 37, pp. 1727- 1739 ,(2008) , 10.1039/B800310F
Grégory Chaume, Marie-Céline Van Severen, Sinisa Marinkovic, Thierry Brigaud, Straightforward Synthesis of (S)- and (R)-α-Trifluoromethyl Proline from Chiral Oxazolidines Derived from Ethyl Trifluoropyruvate Organic Letters. ,vol. 8, pp. 6123- 6126 ,(2006) , 10.1021/OL062593+
Gizem Akçay, Krishna Kumar, A New Paradigm for Protein Design and Biological Self-Assembly Journal of Fluorine Chemistry. ,vol. 130, pp. 1178- 1182 ,(2009) , 10.1016/J.JFLUCHEM.2009.09.002
Mao Liu, Jing Li, Xiao Xiao, Ying Xie, Yian Shi, An efficient synthesis of optically active trifluoromethyl aldimines via asymmetric biomimetic transamination Chemical Communications. ,vol. 49, pp. 1404- 1406 ,(2013) , 10.1039/C2CC37423D