Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

We disclose herein a Au­(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]­nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unp...

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Published inOrganic letters Vol. 23; no. 6; pp. 2279 - 2284
Main Authors Chen, Guzhou, Liu, Peng-Yu, Zou, Huanhuan, Hu, Jiadong, Fang, Xiaowu, Xu, Dongyang, He, Yu-Peng, Wei, Hongbo, Xie, Weiqing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:We disclose herein a Au­(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]­nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00411