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DOI: 10.1055/s-0031-1289535
TiCl4-Promoted Mukaiyama Aldol Reaction of Fluorinated Silyl Enolates for the Construction of a Quaternary Carbon Center
Publication History
Publication Date:
19 October 2011 (online)

Abstract
A method for the preparation of α-fluoro-β-hydroxyphenones from Mukaiyama aldol reactions of various aldehydes and fluorinated silyl enolates was reported. The reaction was promoted by TiCl4 and afforded the desired products in good to excellent yields. The relative stereochemistry of the products was determined by X-ray analysis of single crystals of syn-2-fluoro-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one and anti-2-fluoro-3-hydroxy-2,4,4-trimethyl-1-phenylpentan-1-one.
Key words
aldol reaction - Lewis acids - fluorine - enols - aldehydes
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References and Notes
See Supporting Information for details. The complete crystallographic data can be obtained under the deposition numbers CCDC 833428 from the Cambridge Crystallo-graphic Data Centre.
17See Supporting Information for details. The complete crystallographic data can be obtained under the deposition numbers CCDC 833429 from the Cambridge Crystallo-graphic Data Centre.