4.8 Article

Gold-Catalyzed [4+1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core

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ORGANIC LETTERS
卷 20, 期 13, 页码 3806-3809

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01398

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  1. Ministry of Education, Taiwan [MOE 106N506CE1]
  2. Ministry of Science and Technology, Taiwan [MOST 107-3017-F-007-002]

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This work reports gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles or benzisoxazoles to yield pyrrole derivatives. The reaction chemoselectivity is controlled by an initial attack of an isoxazole at a less hindered alkyne to form gold carbenes, further inducing a 1,2-migration of a second alkyne group. A broad substrate scope of 1,4-diyn-3-ols, isoxazoles and even benzisoxazoles highlighted the reaction utility.

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