Issue 41, 2018, Issue in Progress

Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity

Abstract

To shed light on the influence of reaction parameters on palladium-catalyzed tandem allylic alkylation in the presence of Fei-Phos (a chiral trans-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.

Graphical abstract: Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity

Supplementary files

Article information

Article type
Paper
Submitted
08 Apr 2018
Accepted
12 Jun 2018
First published
22 Jun 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 22944-22951

Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity

P. Long, J. Xu, X. Bai, Z. Xu, Z. Zheng, K. Yang, L. Li and L. Xu, RSC Adv., 2018, 8, 22944 DOI: 10.1039/C8RA02995D

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