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

[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 prod...

Full description

Bibliographic Details
Authors: Pérez Palau, Marina, Sanosa, Nil, Romea, Pedro, Urpí, Félix, López Álvarez, Rosa María, Gómez Bengoa, Enrique, Font Bardia, Mercè
Format: article
Publication Date:2021
Country:España
Institution:Universidad del País Vasco
Repository:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/54216
Online Access:http://hdl.handle.net/10810/54216
Access Level:Open access
Description
Summary:[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.

Similar Items