Synfacts 2011(1): 0047-0047  
DOI: 10.1055/s-0030-1259178
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Lewis Base Catalyzed Asymmetric Selenoetherification

Contributor(s): Mark Lautens, David A. Candito
S. E. Denmark*, D. Kalyani, W. R. Collins
University of Illinois, Urbana, USA
Further Information

Publication History

Publication Date:
21 December 2010 (online)

Significance

Selenofunctionalizations represent an important class of reactions available to the synthetic chemist due to the versatility of the products. The synthesis of enantiomerically enriched products containing selenium has relied on the use of chiral selenylating agents or substrate control, which is not ideal by today’s standards of efficiency and atom economy. The authors report the first Lewis base catalyzed asymmetric selenofunctionalization of unactivated olefins and have carried out detailed mechanistic studies, which shed light on the various elements of the catalytic cycle and pave the way for future reaction design.