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A Chiral <i>N</i>,<i>N′</i>‐Dioxide–Zn<sup>II</sup> Complex Catalyzes the Enantioselective [2+2] Cycloaddition of Alkynones with Cyclic Enol Silyl Ethers
21
Citations
62
References
2016
Year
Chemical EngineeringEngineeringInternal AlkynesNatural SciencesDiversity-oriented SynthesisOrganic ChemistryCatalysisChemistryChiral NFused Cyclobutane DerivativesAsymmetric CatalysisEnantioselective SynthesisBiomolecular Engineering
Abstract A highly efficient enantioselective [2+2] cycloaddition between alkynones and cyclic enol silyl ethers was developed by using a chiral N , N′ ‐dioxide‐zinc(II) complex as a catalyst. This method functions well for a variety of terminal alkynes as well as cyclic enol silyl ethers, with good to excellent enantioselectivity (up to 97 % ee ). This is also the first successful example for the catalytic enantioselective [2+2] cycloaddition of internal alkynes with cyclic enol silyl ethers to give fully substituted cyclobutenes. Meanwhile, the desired cyclobutene product can easily be transformed into fused cyclobutane derivatives.
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