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Stereoselective synthesis of alkylidene phthalides

Dragan, Andrei, Jones, D. Heulyn, Kennedy, Alan R. and Tomkinson, Nicholas C. O. 2016. Stereoselective synthesis of alkylidene phthalides. Organic Letters 18 (13) , pp. 3086-3089. 10.1021/acs.orglett.6b01203

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The N,O-diacylhydroxylamine derivative 4 has been prepared and its reactivity with nucleophiles investigated. On reaction with lithium enolates of cyclic or acyclic ketones, 4 is converted stereoselectively to the corresponding alkylidene phthalide. The stereochemical outcome of the transformation can be modified by changing the polarity of the reaction medium and the products isomerized under acidic conditions.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Biosciences
Publisher: ACS
ISSN: 1523-7060
Last Modified: 29 Feb 2020 16:28

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