Highly Stereoselective [3+2] Cycloadditions of Chiral Palladium‐Containing N1‐1,3‐Dipoles: A Divergent Approach to Enantioenriched Spirooxindoles |
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| Authors: | Tian‐Ren Li Bei‐Yi Cheng Si‐Qi Fan Ya‐Ni Wang Prof. Dr. Liang‐Qiu Lu Prof. Dr. Wen‐Jing Xiao |
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| Affiliation: | 1. CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China;2. Department of Chemistry, University of Oregon, Eugene, OR, USA;3. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, P. R. China |
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| Abstract: | A catalytic asymmetric [3+2] cycloaddition reaction of chiral palladium‐containing N1‐1,3‐dipoles with methyleneindolinones has been successfully developed. The reaction allows an efficient construction of 3,3′‐pyrrolinyl spirooxindoles with high yields and excellent stereoselectivities (up to 93 % yield, 19:1 d.r. and >99 % ee). A synthetic application of this methodology is demonstrated and a stereocontrol mechanism is proposed. |
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| Keywords: | asymmetric catalysis aziridines organic chemistry palladium spirooxindole |
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