Download PDF
Synfacts 2008(8): 0876-0876  
DOI: 10.1055/s-2008-1078538
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Thiourea/DMAP-Catalyzed Cascade Reaction

Contributor(s): Benjamin List, Kristina Zumbansen
L.-Q. Lu, Y.-J. Cao, X.-P. Liu, J. An, C.-J. Yao, Z.-H. Ming, W.-J. Xiao*
Central China Normal University, Wuhan, P. R. of China
Further Information

Publication History

Publication Date:
23 July 2008 (online)

    Permissions and Reprints

Significance

A new organocatalytic cascade reaction of stable sulfur ylides and nitroolefins catalyzed by thiourea 1 and DMAP to afford diverse oxazolidin-2-ones with high diastereoselectivities is reported. The scope of the nitroolefins and the sulfur ylides has been studied. Too stable or too sterically hindered ylides cannot be employed by this protocol. Furthermore a catalytic cycle is proposed that involves intermediates A and B, which is supported by D- and ¹³C-labeling experiments.