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 | Zendy

Jialing Shi | Zendy; Ting Wang | Zendy; Yusha Huang | Zendy; Xinhao Zhang | Zendy; YunDong Wu | Zendy; Qian Cai | Zendy

Open Access

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

Author(s) -

Jialing Shi,

Ting Wang,

Yusha Huang,

Xinhao Zhang,

YunDong Wu,

Qian Cai

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5036613

Subject(s) - chemistry , enantioselective synthesis , intramolecular force , desymmetrization , ligand (biochemistry) , aryl , catalysis , hydroxymethyl , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry , alkyl

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.

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