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First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives

✍ Scribed by Diego J Ramón; Miguel Yus

Book ID
104208551
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
921 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The reaction of diethylzinc or dimethylzinc with prostereogenic ketones, in the presence of a stoichiometric amount of titanium tetraisopropoxide and a catalytic amount (20%) of camphorsulfonamide derivatives as chiral ligands leads to the formation of the corresponding enantioenriched tert-alcohols with enantiomeric ratios up to 94.5 : 5.5. The best results were obtained when phenones are used as substrates independently of the dialkylzinc reagent. The enantioselectivity shows a linear relationship with the enantiomeric excess of the ligand and seems to be independent of the reaction yield. A tentative catalytic cycle and mechanistic model are proposed for this new reaction.

📜 SIMILAR VOLUMES

ChemInform Abstract: First Enantioselect
ChemInform Abstract: First Enantioselective Addition of Diethylzinc and Dimethylzinc to Prostereogenic Ketones Catalyzed by Camphorsulfonamide-Titanium Alkoxide Derivatives.
✍ D. J. RAMON; M. YUS 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

First enantioselective addition of dialk
First enantioselective addition of dialkylzinc to ketones promoted by titanium(IV) derivatives
✍ Diego J. Ramón; Miguel Yus 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 275 KB

The reaction of dimethyl or diethylzinc with ketones in the presence of a stoichiometric amount of titanium tetraisopropoxide and a catalytic amount (20 tool %) of camphorsulfonamide derivatives as chiral ligands leads to the formation of the corresponding enantioenriched alcohols with enantiomeric