期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 3, 页码 1009-1013出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405965
关键词
cycloaddition; gold; homogeneous catalysis; propargyl ester; ynamides
资金
- National Natural Science Foundation of China [21125210, 21372244, 21121062]
- Chinese Academy of Science
- Major State Basic Research Development Program [2011CB808700]
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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