Synfacts 2010(3): 0310-0310  
DOI: 10.1055/s-0029-1219332
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Domino Synthesis of Tricyclic Heterocycles

Contributor(s): Mark Lautens, Jane Panteleev
L.-Q. Lu, F. Li, J. An, J.-J. Zhang, X.-L. An, Q.-L. Hua, W.-J. Xiao*
Central China Normal University, Hubei, P. R. of China
Further Information

Publication History

Publication Date:
18 February 2010 (online)

Significance

This work illustrates the use of sulfur ylides 1 in a formal [4+1] cyclization to nitroolefins 2 yielding an intermediate capable of further [3+2] cycloaddition. The initial addition is based on the group’s earlier work (J. Am. Chem. Soc. 2008, 130, 6946). The resulting products 3 are stereochemically enriched, densely functionalized, and formed as a single diastereomer.