Citation: Shuai Zhu, Mingjie Chen, Haichao Shen, Hanming Ding, Wenbo Li, Junliang Zhang. Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature[J]. Chinese Chemical Letters, ;2024, 35(11): 109879. doi: 10.1016/j.cclet.2024.109879 shu

Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature

Shuai Zhu ^{a, 1} ,
Mingjie Chen ^{a, 1} ,
Haichao Shen ^c ,
Hanming Ding ^{b, **,} ,
Wenbo Li ^{a, **,} ,
Junliang Zhang ^{a, c, *,}

a.
State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
b.
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China
c.
Department of Chemistry, Fudan University, Shanghai 200438, China

^**

hmding@chem.ecnu.edu.cn

wbli@chem.ecnu.edu.cn

junliangzhang@fudan.edu.cn

Received Date: 30 January 2024
Revised Date: 30 March 2024
Accepted Date: 9 April 2024
Available Online: 10 April 2024

Figures(7)

Metal-catalyzed alkene arylalkoxylation is a powerful complexity-building strategy for the synthesis of oxygen heterocycles from simple γ-unsaturated alcohols, but only a few examples of catalytic enantioselective methods exist. Herein, an efficient palladium-catalyzed enantioselective arylalkoxylation of γ-hydroxyalkenes with aryl halides is reported. The salient features of this transformation include a remarkable broad substrate scope, mild reaction conditions, and good functional group tolerance, delivering a series of chiral tetrahydrofurans containing a tertiary or quaternary stereocenter in good yields with up to 95% ee. The Xu10 ligand with a suitable side-arm was responsible for the high reactivity and good enantioselectivity of this transformation.
- Palladium-catalysis,
- Xu-Phos,
- Enantioselective,
- Arylalkoxylation,
- γ-Hydroxyalkenes
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