Dipeptide‐Derived Multifunctional Quaternary Phosphonium Salt Catalyzed Asymmetric Cyclizations via a Tandem Michael Addition/SN2 Sequence
作者： Dongdong Cao , Jiaxing Zhang , Hongyu Wang , Gang Zhao , None
关键词: Tandem 、 Dipeptide 、 Chemistry 、 Phosphonium 、 Organic chemistry 、 SN2 reaction 、 Michael reaction 、 Phosphonium salt 、 Organocatalysis 、 Intramolecular force
摘要: A novel family of dipeptide-based multifunctional quaternary phosphonium salts has been developed as chiral phase-transfer catalysts, which feature ready accessibility and structure modularity, allowing easy fine-tunings activity. They demonstrated high efficiency in catalyzing the tandem asymmetric Michael addition/intramolecular SN 2 reaction between 6 or 7-substituted conjugate enones malonates, providing synthetically important five six-membered carbocycles heterocycles good yields with to excellent enantioselectivities.
sci-hub.se 参考文章(70)
Dongdong Cao, Zhuo Chai, Jiaxing Zhang, Zhengqing Ye, Hua Xiao, Hongyu Wang, Jinhao Chen, Xiaoyu Wu, Gang Zhao, Thiourea-phosphonium salts from amino acids: cooperative phase-transfer catalysts in the enantioselective aza-Henry reaction Chemical Communications. ,vol. 49, pp. 5972- 5974 ,(2013) , 10.1039/C3CC42864H
Chandra M. R. Volla, Iuliana Atodiresei, Magnus Rueping, Catalytic C-C bond-forming multi-component cascade or domino reactions: pushing the boundaries of complexity in asymmetric organocatalysis. Chemical Reviews. ,vol. 114, pp. 2390- 2431 ,(2014) , 10.1021/CR400215U
Hua Xiao, Zhuo Chai, Dongdong Cao, Hongyu Wang, Jinghao Chen, Gang Zhao, Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines Organic and Biomolecular Chemistry. ,vol. 10, pp. 3195- 3201 ,(2012) , 10.1039/C2OB25295C
Xun-Xiang Guo, Da-Wei Gu, Zhengxing Wu, Wanbin Zhang, Copper-catalyzed C-H functionalization reactions: efficient synthesis of heterocycles. Chemical Reviews. ,vol. 115, pp. 1622- 1651 ,(2015) , 10.1021/CR500410Y
Peng Fu, Marc L. Snapper, Amir H. Hoveyda, Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines. Journal of the American Chemical Society. ,vol. 130, pp. 5530- 5541 ,(2008) , 10.1021/JA8001343
Laura C. Wieland, Erika M. Vieira, Marc L. Snapper, Amir H. Hoveyda, Ag-Catalyzed Diastereo- and Enantioselective Vinylogous Mannich Reactions of α-Ketoimine Esters. Development of a Method and Investigation of its Mechanism Journal of the American Chemical Society. ,vol. 131, pp. 570- 576 ,(2009) , 10.1021/JA8062315
Youming Huang, Changwu Zheng, Zhuo Chai, Gang Zhao, Synthesis of Spiro[chroman/tetrahydrothiophene-3,3 '-oxindole] Scaffolds via Heteroatom-Michael-Michael Reactions: Easily Controlled Enantioselectivity via Bifunctional Catalysts Advanced Synthesis & Catalysis. ,vol. 356, pp. 579- 583 ,(2014) , 10.1002/ADSC.201300833
Takashi Ooi, Daisuke Ohara, Kazuhiro Fukumoto, Keiji Maruoka, Importance of Chiral Phase-Transfer Catalysts with Dual Functions in Obtaining High Enantioselectivity in the Michael Reaction of Malonates and Chalcone Derivatives Organic Letters. ,vol. 7, pp. 3195- 3197 ,(2005) , 10.1021/OL050902A
Jinhao Chen, Yuepeng Cai, Gang Zhao, Asymmetric Michael Addition of Oxindoles to Allenoate Catalyzed by N‐Acyl Aminophosphine: Construction of Functionalized Oxindoles with Quaternary Stereogenic Center Advanced Synthesis & Catalysis. ,vol. 356, pp. 359- 363 ,(2014) , 10.1002/ADSC.201300695
Xiaoyu Wu, Qin Liu, Yong Liu, Qun Wang, Ying Zhang, Jie Chen, Weiguo Cao, Gang Zhao, None, Amino Acid-Derived Phosphonium Salts-Catalyzed Michael Addition of 3-Substituted Oxindoles Advanced Synthesis & Catalysis. ,vol. 355, pp. 2701- 2706 ,(2013) , 10.1002/ADSC.201300383