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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
Author(s) -
Liu Jun,
Chen Ming,
Zhang Liangwei,
Liu Yuanhong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405965
Subject(s) - cycloisomerization , chemistry , propargyl , moiety , cycloaddition , isomerization , triple bond , indole test , catalysis , stereochemistry , carbenoid , medicinal chemistry , double bond , combinatorial chemistry , organic chemistry , rhodium
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.