Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes |
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| Institution: | 1. School of Life Science, Changchun Normal University, Changchun 130032, China;2. College of Chemistry and Chemical Engineering, Zhoukou Normal University, Zhoukou 466000, China;3. Key Laboratory of Grain and Oil Processing of Jilin Province, Jilin Business and Technology College, Changchun 130507, China;1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;2. Molecular & Structural Biology Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;3. Academy of Scientific and Innovative Research, New Delhi, India;1. Department of Chemistry, Section for Chemical Biology and Nanobioscience, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark;2. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Denmark;3. CNRS, UMR 6296, ICCF, BP 80026, 63171 Aubière, France;4. Clermont Université, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand, BP 10448, 63000 Clermont-Ferrand, France |
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| Abstract: | Six chiral amino sulfides have been synthesised from the amino acids phenylalanine, phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with benzaldehyde, resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of >98.5 and 95%, respectively. These stereoselectivities were significantly higher than those induced by the ether analogues. |
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