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Diastereoselectivity in the directed aldol reactions of 1-fluoro-3,3-dimethyl-butanone enolates and enol silyl ethers.

✍ Scribed by John T. Welch; Karl W. Seper

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 217 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81575-6

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✦ Synopsis

High diastereoselectivity was observed in the directed aldol reaction of lithiun 'enolates of 1-fluoro-3,3_dimethylbutanone while an apparent reversa1 of diastereoselection was found in Lewis acid mediated reactions of corresponding enol silyl ethers. Application of the directed aldol reaction' to a-fluorinated enolates would provide a convenient route to the stereoselective synthesis of a variety of specifically fluorinated molecules. Halogenated enolates2 and fluorinated enolates3 have been reported, but, with few

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