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Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides.

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Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the… Click to show full abstract

Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.

Keywords: titanium enolates; alkylation; stereoselective decarboxylative; diacyl peroxides; enolates diacyl

Journal Title: Organic letters
Year Published: 2019

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