4.8 Article

Enantioselective Gold(I)-Catalyzed Heterocyclization-Intermolecular Exo [4+3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes

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ORGANIC LETTERS
卷 21, 期 9, 页码 3018-3022

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00537

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  1. Shanghai Sailing Program [16YF1402800]
  2. 973 Programs [2015CB856600]
  3. National Natural Science Foundation of China [21672067, 21702063]
  4. Changjiang Scholars and Innovative Research Team in University (PCSIRT)

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The highly exo- and enantioselective gold-catalyzed tandem heterocyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran was implemented by utilizing Ming-Phos, which provides a facile access to chiral seven-membered oxa-bridged rings in 80-98% yield with high exo selectivity (exo/endo up to 50:1) and up to 97% ee.

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