Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters†
Jin-Sheng Yu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorFu-Min Liao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorWei-Ming Gao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorKui Liao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorRun-Lin Zuo
No 15 class of Grade 2012, Luzhou High School, 33 Zhongshan Road, Luzhou 646000 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jian Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (P.R. China)
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)Search for more papers by this authorJin-Sheng Yu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorFu-Min Liao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorWei-Ming Gao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorKui Liao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
Search for more papers by this authorRun-Lin Zuo
No 15 class of Grade 2012, Luzhou High School, 33 Zhongshan Road, Luzhou 646000 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jian Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (P.R. China)
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)Search for more papers by this authorWe acknowledge financial support from the 973 program (2011CB808600), NSFC (21222204, 21472049), Ministry of Education (NCET-11-0147 and PCSIRT), and Program of SSCS (13XD1401600).
Graphical Abstract
Four C′s: The chiral secondary amine phosphoramide A was developed and serves as a powerful catalyst for the Michael addition of fluorinated enol silyl ethers to tetrasubstituted olefins. The resulting products are obtained with high enantioselectivities and contain a quaternary carbon stereocenter bearing either a difluoroalkyl or monofluoroalkyl group. TMS=trimethylsilyl.
Abstract
A chiral secondary amine phosphoramide was developed and identified as a powerful catalyst for the Mukaiyama–Michael addition of fluorinated enol silyl ethers to tetrasubstituted olefins. The resulting products are obtained with high enantioselectivities and contain a quaternary carbon stereocenter bearing either a difluoroalkyl or monofluoroalkyl group.
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- 27CCDC 1047041 (5 b), CCDC 1047043 (6), CCDC 1047044 (10), and CCDC 1047042 (12) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
