Organic Letters
Organic Letters
5 years ago

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

Stereoselective Access to Alkylidenecyclobutanes through γ-Selective Cross-Coupling Strategies
Dorian Didier, Michael Eisold
Alkylidenecyclobutanes (ACBs) containing all-carbon quaternary stereocenters were simply and efficiently synthesized by combining boron-homologation and γ-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 γ-selective cross-coupling reactions is finally shown.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01803

DOI: 10.1021/acs.orglett.7b01803

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