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Synfacts 2016; 12(2): 0171
DOI: 10.1055/s-0035-1561173
DOI: 10.1055/s-0035-1561173
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Copper-Catalyzed Asymmetric Ring Opening of D–A Cyclopropanes
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 H2O-Nucleophilic Ring Opening of D–A Cyclopropanes: Catalyst Serves as a Source of Water.
J. Am. Chem. Soc. 2015;
137: 14594-14597
Asymmetric H2O-Nucleophilic Ring Opening of D–A Cyclopropanes: Catalyst Serves as a Source of Water.
J. Am. Chem. Soc. 2015;
137: 14594-14597
Further Information
Publication History
Publication Date:
19 January 2016 (online)
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).
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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.
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