Gold(I)‐Catalyzed 1,2‐Acyloxy Migration/[3+2] Cycloaddition of 1,6‐Diynes with an Ynamide Propargyl Ester Moiety: Highly Efficient Synthesis of Functionalized Cyclopenta[b]indoles |
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| Authors: | Dr. Jun Liu Ming Chen Liangwei Zhang Prof. Yuanhong Liu |
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| Affiliation: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P. R. China);2. Center of Drug Discovery, College of Pharmacy, China Pharmaceutical University, 24 Tongjia Xiang Road, Nanjing 210009 (P. R. China) |
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| Abstract: | A gold‐catalyzed cycloisomerization of 1,6‐diynes containing an ynamide propargyl ester or carbonate moiety has been developed that provides an attractive route to a diverse‐substituted 3‐acyloxy‐1,4‐dihydrocyclopenta[b]indoles. Mechanistic studies indicate that the reaction likely proceeds through a competitive 1,2‐OAc migration followed by [3+2] cycloaddition of the vinyl gold–carbenoid intermediate with the pendant triple bond. The synthetic utility of the obtained cyclopenta[b]indole products was demonstrated by their efficient transformations by deprotection or double‐bond isomerization reactions. |
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| Keywords: | cycloaddition gold homogeneous catalysis propargyl ester ynamides |
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