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Chiral ligands derived from abrine. Part 5: Substituent effects on asymmetric induction in enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral oxazolidines possessing an indole moiety
Affiliation:1. School of Environmental and Civil Engineering, Jiangnan University, Wuxi 214122, China;2. Suzhou Institute of Environmental Sciences, Postdoctoral Innovation and Practice Base of Jiangsu Province, Suzhou 21500, China;3. Department of Environmental Engineering, College of Environmental and Resource Sciences, Zhejiang University, Hangzhou 310058, China;4. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China;5. College of Environment, Zhejiang University of Technology, Hangzhou 310014, China;1. Department of Emergency Medicine, Oregon Health & Science University, Portland, OR, USA;2. Department of Emergency Medicine, Emergency Medicine Toxicology Fellowship, OHSU, Portland, OR, USA;3. Washington Poison Center, Department of Emergency Medicine, University of Washington, Seattle, WA, USA;4. Washington Poison Center, Medical Toxicology, Department of Emergency Medicine, University of Washington, Seattle, WA, USA
Abstract:A number of the indole-containing chiral oxazolidines possessing the gem-di-p-tolyl and gem-di-o-tolyl groups at C5 were synthesized from abrine and the effects of the C5 and C2 substituents on the asymmetric induction in catalytic enantioselective addition of diethylzinc to benzaldehyde were examined. A working model is proposed to rationalize the asymmetric catalysis by these chiral oxazolidines.
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