New chiral amino-phosphite and phosphite-phosphoroamidite ligands for the copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclohexenone |
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| Affiliation: | 1. Key Laboratory of Yangtze River Water Environment, Ministry of Education, College of Environmental Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, PR China;2. Shanghai Institute of Pollution Control and Ecological Security, 1239 Siping Road, Shanghai 200092, PR China;3. Shanghai Honess Environmental tech Corp., 11 Guotai Road, Shanghai 200092, PR China |
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| Abstract: | We have designed a series of amino-phosphite and phosphite-phosphoroamidite ligands 1–6 derived from inexpensive d-(+)-xylose. These ligands were screened in the Cu-catalyzed asymmetric 1,4-addition of diethylzinc to cyclohexenone. High reaction rates (TOF >1200 h−1) and moderate enantioselectivities (up to 63% e.e.) were obtained. The results showed that the configuration of the stereogenic carbon atom C(3) at the ligand backbone and the different substituents at the amino group had remarkable effects on the activity and enantioselectivity. |
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