Beilstein Journal of Organic Chemistry (Aug 2011)

Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones

  • Ya-Ping Xiao,
  • Xin-Yuan Liu,
  • Chi-Ming Che

DOI
https://doi.org/10.3762/bjoc.7.126
Journal volume & issue
Vol. 7, no. 1
pp. 1100 – 1107

Abstract

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The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction conditions and the substrate scope of this reaction are examined, and a possible mechanism involving AgClO4 catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed.

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