Stereoselective olefin isomerization leading to asymmetric quaternary carbon construction |
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Authors: | Wang Kan Bungard Christopher J Nelson Scott G |
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Institution: | Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. |
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Abstract: | Chemo- and stereoselective Ir(I)-catalyzed isomerization of 1,1-disubstituted and trisubstituted allylic ethers and in situ 3,3] sigmatropic rearrangement of the resulting allyl vinyl ethers provide for the highly stereoselective construction of quaternary carbon stereocenters. The olefin isomerization-Claisen rearrangement (ICR) sequence allows adjacent quaternary-tertiary stereocenter relationships to be established with excellent diastereoselection. Several complementary strategies for enantioselective quaternary carbon synthesis derive directly from the ICR reaction design. |
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