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One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers

Junghyun Chae, Jaesook Yun and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

J. Chae, J. Yun, S. L. Buchwald, Org. Lett., 2004, 6, 4809-4812.

DOI: 10.1021/ol048313c (free Supporting Information)


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Abstract

Cu-catalyzed asymmetric conjugate reduction of β-substituted ketones leads to enantiomerically enriched diphenylsilyl enol ethers, which are utilized in a diastereoselective Pd-catalyzed α-arylation of various aryl bromides to yield disubstituted cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The procedure can be carried out in one-pot.

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Key Words

Diphenylsilane, Copper Hydride, conjugate Reduction, α-Arylation, Cyclopentanones


ID: J54-Y2004-1230