Catalytic enantioselective chlorination and bromination of β-keto esters

Lukas Hintermann, Antonio Togni

Research output: Contribution to journalArticlepeer-review

132 Scopus citations

Abstract

The Ti(TADDOLato) complexes dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dim ethanolato(2 -)-O,O']titanium ((R)-1a) and dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetra(naphthalen-1-yl)-1,3-dioxol ane-4,5-dimethanolato(2-)-O,O']titanium ((R)-1b) are efficient catalysts for the electrophilic enantioselective chlorination and bromination of β-keto esters with N-chlorosuccinimide (NCS) and N-bromosuccinimide (NBS), respectively. With 5 mol-% of catalyst at room temperature an enantioselectivity of up to 88% ee could be obtained for the chlorination reaction. Under comparable conditions, bromination reactions are slower and less stereoselective.

Original languageEnglish
Pages (from-to)2425-2435
Number of pages11
JournalHelvetica Chimica Acta
Volume83
Issue number9
DOIs
StatePublished - 2000
Externally publishedYes

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