Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 18, Pages 5541-5544Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600801
Keywords
[2+2] cycloaddition; asymmetric catalysis; cycloaddition; N-N'-dioxides; synthetic methods
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Funding
- National Natural Science Foundation of China [21432006, 21372162]
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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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