Stereoselective palladium-catalyzed carboetherification of cyclopropenes via a tethering strategy
Duncan K. Brownsey, Alexandre A. Schoepfer, Jerome Waser
TL;DR
This paper introduces a new palladium-catalyzed method to create complex cyclopropane structures with high selectivity and efficiency.
Contribution
The first stereoselective carboetherification of cyclopropenes using a palladium-catalyzed tethering strategy.
Findings
The reaction produces pentasubstituted spirocyclopropanes as single diastereoisomers.
It is compatible with various functional groups and can be scaled up to gram quantities.
Product modifications are possible through acid-mediated ring-opening or by accessing free alcohols and amines.
Abstract
Highly functionalized cyclopropanes are often sought after chemical motifs as building blocks in synthetic and medicinal chemistry. However, their stereoselective synthesis using catalytic methods remains a challenge. Herein we report the first carboetherification of cyclopropenes using a palladium-catalyzed tethering strategy. This reaction was compatible with various functional groups, and could be performed using aryl, alkynyl and vinyl coupling partners. The carboetherification proceeded in a stereoselective manner imparted by the trifluoromethylated tether and afforded pentasubstituted spirocyclopropanes as single diastereoisomers, extending significantly the scope of metal-catalyzed difunctionalization of strained alkenes. This process could be easily scaled up to a gram scale, and product modifications were enabled either by acid mediated ring-opening or by accessing free…
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Taxonomy
TopicsCyclopropane Reaction Mechanisms · Catalytic C–H Functionalization Methods · Catalytic Alkyne Reactions