Highly organocatalytic asymmetric Michael–ketone aldol–dehydration domino reaction: straightforward approach to construct six-membered spirocyclic oxindoles
作者： Liang-Liang Wang , Lin Peng , Jian-Fei Bai , Qing-Chun Huang , Xiao-Ying Xu
DOI: 10.1039/C0CC03032E
关键词:
摘要: An efficient Michael–ketone aldol–dehydration domino reaction has been developed to afford spiro[cyclohex-2-enone-oxindole] motifs with high yields (up 99%), excellent diastereoselectivities (dr >20 : 1) and enantioselectivities 96% ee).
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Andrew Fensome, William R. Adams, Andrea L. Adams, Tom J. Berrodin, Jeff Cohen, Christine Huselton, Arthur Illenberger, Jeffrey C. Kern, Valerie A. Hudak, Michael A. Marella, Edward G. Melenski, Casey C. McComas, Cheryl A. Mugford, Ov D. Slayden, Matthew Yudt, Zhiming Zhang, Puwen Zhang, Yuan Zhu, Richard C. Winneker, Jay E. Wrobel, Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348). Journal of Medicinal Chemistry. ,vol. 51, pp. 1861- 1873 ,(2008) , 10.1021/JM701080T
Amy B. Dounay, Larry E. Overman, The asymmetric intramolecular Heck reaction in natural product total synthesis. Chemical Reviews. ,vol. 103, pp. 2945- 2964 ,(2003) , 10.1021/CR020039H
Daiki Hojo, Keiichi Noguchi, Masao Hirano, Ken Tanaka, Enantioselective Synthesis of Spirocyclic Benzopyranones by Rhodium‐Catalyzed Intermolecular [4+2] Annulation Angewandte Chemie. ,vol. 47, pp. 5820- 5822 ,(2008) , 10.1002/ANIE.200801642
Jacek Mlynarski, Joanna Paradowska, Catalytic asymmetric aldol reactions in aqueous media Chemical Society Reviews. ,vol. 37, pp. 1502- 1511 ,(2008) , 10.1039/B710577K
Andrew Madin, Christopher J. O'Donnell, Taeboem Oh, David W. Old, Larry E. Overman, Matthew J. Sharp, Use of the Intramolecular Heck Reaction for Forming Congested Quaternary Carbon Stereocenters. Stereocontrolled Total Synthesis of (±)-Gelsemine Journal of the American Chemical Society. ,vol. 127, pp. 18054- 18065 ,(2005) , 10.1021/JA055711H
Hariharan Venkatesan, Matthew C. Davis, Yesim Altas, James P. Snyder, Dennis C. Liotta, Total Synthesis of SR 121463 A, a Highly Potent and Selective Vasopressin V2 Receptor Antagonist Journal of Organic Chemistry. ,vol. 66, pp. 3653- 3661 ,(2001) , 10.1021/JO0004658
Kun Jiang, Jing Peng, Hai-Lei Cui, Ying-Chun Chen, Organocatalytic asymmetric allylic alkylation of oxindoles with Morita–Baylis–Hillman carbonates Chemical Communications. pp. 3955- 3957 ,(2009) , 10.1039/B905177E
Gabriela Guillena, Carmen Nájera, Diego J. Ramón, Enantioselective direct aldol reaction: the blossoming of modern organocatalysis Tetrahedron-asymmetry. ,vol. 18, pp. 2249- 2293 ,(2007) , 10.1016/J.TETASY.2007.09.025
Natalia Bravo, Ignasi Mon, Xavier Companyó, Andrea-Nekane Alba, Albert Moyano, Ramon Rios, Enantioselective addition of oxindoles to aliphatic α,β-unsaturated aldehydes Tetrahedron Letters. ,vol. 50, pp. 6624- 6626 ,(2009) , 10.1016/J.TETLET.2009.09.038
Xin Li, Bo Zhang, Zhi-Guo Xi, Sanzhong Luo, Jin-Pei Cheng, Asymmetric Michael Addition Reaction of 3‐Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Alkyl‐ Substituted Thiourea Catalyst Advanced Synthesis & Catalysis. ,vol. 352, pp. 416- 424 ,(2010) , 10.1002/ADSC.200900630