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Org Lett. 2004 Dec 23;6(26):4809-12.

One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers.

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1
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Abstract

[reaction: see text] Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.

PMID:
15606072
DOI:
10.1021/ol048313c
[Indexed for MEDLINE]
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