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Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters.

ABSTRACT: Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-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.

SUBMITTER: Perez-Palau M

PROVIDER: S-EPMC8609576 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters.

Pérez-Palau Marina M Sanosa Nil N Romea Pedro P Urpí Fèlix F López Rosa R Gómez-Bengoa Enrique E Font-Bardia Mercè M

Organic letters 20211026 22

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-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 compo ...[more]

PMID: 34699246

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