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:10.3762/bjoc.7.126

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

Beilstein J Org Chem. 2011:7:1100-7. doi: 10.3762/bjoc.7.126. Epub 2011 Aug 11.

Authors

Ya-Ping Xiao¹, Xin-Yuan Liu, Chi-Ming Che

Affiliation

¹ Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 , P. R. China.

Abstract

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 AgClO(4) catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed.

Keywords: cascade; cocatalyzed; gold(I)-catalyzed; intermolecular N-Michael addition; intramolecular hydroalkylation; pyrrolidine; silver(I)-catalyzed.