Phosphoramidite Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of 3,4-Substituted Pyrrolidines

• DOI: 10.1021/ja200084a
• Publication Date: 2011-03-23T16:10:03Z
• Authors: Ana Z. González; Diego Benitez; Ekaterina Tkatchouk; William A. Goddard; F. Dean Toste
• Keywords: Phosphoramidite; Stereocenter

In this article the utility of phosphoramidite ligands in enantioselective Au(I) catalysis was explored development highly diastereo- and Au(I)-catalyzed cycloadditions allenenes. A synthesis 3,4-disubstituted pyrrolidines γ-lactams is described. This reaction proceeds through cyclization allenenes to form a carbocationic intermediate that trapped by an exogenous nucleophile, resulting diastereoselective construction three contiguous stereogenic centers. computational study (DFT) also performed gain some insight into underlying mechanisms these cycloadditions. The new methodology demonstrated formal (-)-isocynometrine.