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Synfacts 2006(2): 0119-0119
DOI: 10.1055/s-2005-924828
DOI: 10.1055/s-2005-924828
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Functionalized 2,3-Indoline-Fused Cyclobutanes
L. Zhang*
University of Nevada, Reno, USA
Further Information
Publication History
Publication Date:
23 January 2006 (online)
Significance
The synthesis of 2,3-indoline-fused cyclobutanes from indole-3-acetates under Au(I) catalysis is reported. The reaction, proposed to involve Au activation by acetylene complexation and in situ allenylic ester formation (isolated and characterized by 1H NMR), and finally formal [2+2] cycloaddition, proceeds in good to excellent yields for several substrates. The overall reaction involves the formation of two new C-C bonds and incorporates reactive lactone and olefinic functionality in the final products.