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American Chemical Society, Organic Letters, 4(17), p. 840-843, 2015

DOI: 10.1021/ol5036613

Wiley-VCH Verlag, ChemInform, 28(46), p. no-no, 2015

DOI: 10.1002/chin.201528223

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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

Journal article published in 2015 by Jialing Shi, Ting Wang, Yusha Huang, Xinhao Zhang ORCID, Yun-Dong Wu, Qian Cai
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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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.