Synthesis of novel N,P chiral ligands for palladium-catalyzed asymmetric allylations: the effect of binaphthyl backbone on the enantioselectivity |
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| Affiliation: | 1. Sydney Pharmacy School, The University of Sydney, Sydney, New South Wales 2006, Australia;2. Microbiology Department, Freeman Hospital, Newcastle upon Tyne NE7 7DN, UK;3. School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia;1. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China;2. Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Zigong 643000, China |
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| Abstract: | A series of novel chiral aminophosphine ligands with a 5,5,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl backbone (H8-MAPs) have been synthesized. The application of these ligands in asymmetric allylic substitutions was examined and higher enantioselectivity was observed than that by using the parent ligand (MAP). Under the optimized conditions, the allylation product can be obtained in up to 90.9% ee with H8-MAP having 3,5-xylyls as chiral inducer. The dramatic effect of the binaphthyl backbone on the enantioselectivity of the reaction can be attributed to the change of the bite angle in H8-MAPs/Pd complexes. |
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