Intramolecular [4+2] Cycloaddition of Nitroalkenes

S. E. Denmark; R. Y. Baiazitov

doi:10.1055/s-2005-924781

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Synfacts 2006(2): 0135-0135
DOI: 10.1055/s-2005-924781

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Intramolecular [4+2] Cycloaddition of Nitroalkenes

Contributor(s): Mark Lautens, Josephine Yuen
S. E. Denmark*, R. Y. Baiazitov
University of Illinois, Urbana, USA

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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Intramolecular [4+2] cycloaddition of a nitroalkene catalyzed by SnCl₄ generated two vicinal quaternary stereocenters. This model study was investigated as part of a planned synthesis of daphnilactone B in which the key step is a tandem intramolecular [4+2]/[3+2] cycloaddition.