Synfacts 2011(12): 1333-1333  
DOI: 10.1055/s-0031-1289366
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cu(I)/BINAP-Catalyzed Synthesis of Pyro-glutamates

Contributor(s): Mark Lautens, Patrick T. Franke
H.-L. Teng, F.-L. Luo, H.-Y. Tao, C.-J. Wang*
Wuhan University and Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
18 November 2011 (online)

Significance

A facile protocol for the rapid construction of pyroglutamate derivatives is reported. A Cu(I)/BINAP-catalyzed tandem Michael addition-elimination sequence followed by deprotection-lactamization affords the products bearing a quaternary stereogenic center in good yields with high enantioselectivities. The general reaction scale for this transformation is 0.3 mmol.