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RESEARCH FRONT
Contents Vol 62(7)

Gold Catalysis: Chemoselective Indolin Synthesis in the Presence of Acrylate Units

A. Stephen K. Hashmi A B , Sebastian Wagner A and Frank Rominger A
+ Author Affiliations
- Author Affiliations

A Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

B Corresponding author. Email: hashmi@hashmi.de

Australian Journal of Chemistry 62(7) 657-666 https://doi.org/10.1071/CH09174
Submitted: 26 March 2009  Accepted: 7 April 2009   Published: 13 July 2009

Abstract

A sequence of an aza-Morita–Baylis–Hillman reaction, a simple sulfonamide propargylation, and a gold-catalyzed cycloisomerization delivers indoline derivatives with acrylate units in the side chain. The chemoselectivity in the last step is very high; out of the two C–C double bonds that are in equal distance to the alkyne, only the furan reacts, the acrylate neither participates in nor interferes with the gold catalysis.


Acknowledgements

This work was supported by the Deutsche Forschungsgemeinschaft (HA 1932/10–1). We are grateful to Umicore AG & Co. KG for the donation of gold salts.


References


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