title: Pd-catalyzed asymmetric intramolecular aryl C-O bond formation with SDP(O) ligand: enantioselective synthesis of (2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanols.
abstract: Employing a chiral spirodiphosphine monoxide ligand with 1,1'-spirobiindane backbone (SDP(O)), a desymmetrization strategy of Pd-catalyzed intramolecular asymmetric aryl C-O coupling of 2-(2-halophenoxy)propane-1,3-diols, was developed. The SDP(O) ligand shows much better results than its SDP counterpart. The protocol provides an efficient and highly enantioselective method for the synthesis of 2-hydroxymethyl-1,4-benzodioxanes. Density functional theory studies provide a model that accounts for the origin of the enantioselectivity.
authors: Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou, 510530, China.
authors: Jialing
authors: J
authors: Shi
authors: Ting
authors: T
authors: Wang
authors: Yusha
authors: Y
authors: Huang
authors: Xinhao
authors: X
authors: Zhang
authors: Yun-Dong
authors: YD
authors: Wu
authors: Qian
authors: Q
authors: Cai
mesh_terms: D002384:Catalysis; D004147:Dioxins / Q000138:chemical synthesis* / Q000737:chemistry; D007189:Indans / Q000737:chemistry*; D008024:Ligands; D000432:Methanol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004147:Dioxins; D007189:Indans; D008024:Ligands; D010165:Palladium; D000432:Methanol