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Synfacts 2008(9): 0945-0945  
DOI: 10.1055/s-2008-1078636
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereocontrolled Thermal Pericyclic Cascade Rearrangement

Contributor(s): Mark Lautens, Praew Thansandote
S. E. Steinhardt, J. S. Silverston, C. D. Vanderwal*
University of California at Irvine, USA
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Publikationsdatum:
22. August 2008 (online)

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Significance

While attempting a proposed step in an alkaloid total synthesis, the authors discovered a novel pericyclic cascade involving two 6p-electrocyclization-ring-opening reactions and a [1,5]-hydrogen shift. Various 5-amino-2,4-pentadienals (or Zincke aldehydes) rearranged in this manner to form Z-a,b,g,d-unsaturated amides in moderate to good yields and good diastereoselectivities. The products can be manipulated to convert into alcohols or undergo cross-metathesis with other alkenes.