Kang Q.-K, Wang L, Liu Q.-J, Li J.-F, Tang Y * Shanghai Institute of Organic Chemistry
and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin,
P. R. of China
Asymmetric H
2O-Nucleophilic Ring Opening of D–A Cyclopropanes: Catalyst Serves as a Source of Water.
J. Am. Chem. Soc. 2015;
137: 14594-14597
Key words
ring opening - cyclopropanes - copper - asymmetric catalysis
Significance
The authors report a copper-catalyzed enantioselective ring-opening reaction of donor–acceptor
cyclopropanes with water. A variety of ring-opening products were obtained in high
yields (≤96%) and enantioselectivities (≤95% ee).
Comment
In this reaction, the copper hydrate serves as both a Lewis acid and a source of water;
this affords a system for the controlled release of the appropriate amount of water
as a nucleophile in the asymmetric catalysis. The method provides a new and efficient
approach for direct access to γ-substituted γ-hydroxybutyric acid derivatives.
