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Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction

Xiang Wu, Hua-Chen Lin, Ming-Li Li, Lu-Lu Li, Zhi-Yong Han and Liu-Zhu Gong*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: gonglzustc.edu.cn

X. Wu, H.-C. Lin, M.-L. Li, L.-L. Li, Z.-Y. Han, L.-Z. Gong, J. Am. Chem. Soc., 2015, 137, 13467-13479.

DOI: 10.1021/jacs.5b08734 (free Supporting Information)


Abstract

The use of a H8-BINOL-based phosphoramidite ligand enables a Pd-catalyzed highly enantioselective three-component coupling of 1,3-dienes with aryl iodines and sodium dialkyl malonates via a Pd-catalyzed cascade arylation and asymmetric allylic alkylation reaction. This reaction provides an efficient strategy for the enantioselective 1,2-difunctionalization of 1,3-dienes.

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Key Words

active methylene compounds, arenes, multicomponent reactions


ID: J48-Y2015