A novel, C2-symmetric, chiral bis-cyclosulfinamide-olefin tridentate ligand in Rh-catalyzed asymmetric 1,4-additions

被引：20
作者：
Zhang, Li [1 ]
Tan, Mingchao [1 ]
Zhou, Lihong [2 ]
Zeng, Qingle [1 ]
机构：
[1] Chengdu Univ Technol, Coll Mat Chem & Chem Engn, State Key Lab Geohazard Prevent & Geoenvironm Pro, 1 Dongsanlu, Chengdu 610059, Sichuan, Peoples R China
[2] Chengdu Univ Technol, Coll Environm & Ecol, 1 Dongsanlu, Chengdu 610059, Sichuan, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 29期
关键词：
Asymmetric catalysis; Chiral tridentate ligand; Bis-cyclosulfinamide; 1-Oxo-2,3-dihydro-1,2-benzisothiazole; Asymmetric 1,4-addition; HOMOLYTIC SUBSTITUTION; KINETIC RESOLUTION; SULFOXIDE LIGANDS; SULFUR-OLEFINS; SULFINAMIDES; COMPLEXES; KETIMINES; DIENE; ACIDS;
D O I：
10.1016/j.tetlet.2018.06.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A C-2-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 H-1 NMR analyses verify that the in situ-generated complex of the ligand and [Rh(C2H4)(2)Cl](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. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2778 / 2783
页数：6
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