Stereoselective Access to Alkylidenecyclobutanes through gamma-Selective Cross-Coupling Strategies

Eisold, Michael and Didier, Dorian (2017): Stereoselective Access to Alkylidenecyclobutanes through gamma-Selective Cross-Coupling Strategies. In: Organic Letters, Vol. 19, No. 15: pp. 4046-4049

Abstract

Alkylidenecyclobutanes (ACBs) containing all carbon quaternary stereocenters were simply and efficiently synthesized by combining boron-homologation and gamma-selective cross-coupling strategies. This unique sequence led to excellent regio- and diastereoselectivities in the generation of targeted four-membered rings with up to 99% enantiomeric excess using chiral substrates. In addition to the original synthesis of ACBs, the first asymmetric catalytic formation of quaternary stereocenters based on gamma-selective cross-coupling reactions is finally shown.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English