A novel,C2-symmetric,chiral bis-cyclosulfinamide-olefin tridentate ligand in Rh-catalyzed asymmetric 1,4-additions |
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| Authors: | Li Zhang Mingchao Tan Lihong Zhou Qingle Zeng |
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| Affiliation: | 1. State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (Chengdu University of Technology), Chengdu University of Technology, College of Materials, Chemistry & Chemical Engineering, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, PR China;2. Chengdu University of Technology, College of Environment and Ecology, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, PR China |
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| Abstract: | A C2-symmetric, chiral bis-cyclosulfinamide-olefin ligand composed of two 1-oxo-2,3-dihydro-1,2-benzisothiazole moieties with rigid skeletons and a conformationally flexible butenylene chain is disclosed for the first time. HRMS and 1H NMR analyses verify that the in situ-generated complex of the ligand and [Rh(C2H4)2Cl]2 possesses a rhodium (I) center coordinated to the tridentate ligand via two sulfinyl moieties and a CdbndC bond. The chiral ligand provided extremely high enantioselectivity (up to >99%ee) in the Rh-catalyzed asymmetric 1,4-additions of arylboronic acids to cyclohexenone and cyclopentenone. The tridentate ligand gave much higher enantioselectivity than the analogous chiral bidentate ligands. |
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| Keywords: | Asymmetric catalysis Chiral tridentate ligand Bis-cyclosulfinamide 1-Oxo-2,3-dihydro-1,2-benzisothiazole Asymmetric 1,4-addition OIIBYKBJPMVAST-PESMWXFUSA-N CKDBPHXKIGVKRP-ZEQRLZLVSA-N OKKIKRICMVKKHG-ZFTMLNQLSA-N |
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