Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters
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Date
2021-11-19Author
Pérez Palau, Marina
Sanosa, Nil
Romea, Pedro
Urpí, Félix
López Álvarez, Rosa María
Gómez Bengoa, Enrique
Font Bardia, Mercè
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Organic Letters 23(22) : 8852-8856 (2021)
Abstract
[EN]Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Calpha-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.