Palladium-catalyzed Tandem Allylic Substitution/cyclization and Cascade Hydrosilylated Reduction: the Influence of Reaction Parameters and Hydrosilanes on the Stereoselectivity

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 11

PMID 35540169

Authors

Peng-Wei Long

Jian-Xing Xu

Xing-Feng Bai

Zheng Xu

Zhan-Jiang Zheng

Ke-Fang Yang

Li Li

Li-Wen Xu

Affiliations

Soon will be listed here.

Abstract

To shed light on the influence of reaction parameters on palladium-catalyzed tandem allylic alkylation in the presence of Fei-Phos (a chiral -1,2-diaminocyclohexane-derived phosphine ligand), the effect of different phosphine ligands, inorganic or organic bases, Brønsted acids, and other additives on the asymmetric palladium-catalysed alkylation of catechol with allylic diacetate was investigated. In this reaction, 2-vinyl-2,3-dihydro-benzo[1,4]dioxin products with promising enantioselectivity were achieved in good yields. In addition, a novel palladium-catalyzed three-component and one-pot allylic substitution/cyclization/reduction reaction assisted by methylphenylsilane was reported with good selectivity.

Citing Articles

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.

Pamies O, Margalef J, Canellas S, James J, Judge E, Guiry P Chem Rev. 2021; 121(8):4373-4505.

PMID: 33739109 PMC: 8576828. DOI: 10.1021/acs.chemrev.0c00736.

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