Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2008(9): 0945-0945
DOI: 10.1055/s-2008-1078636
DOI: 10.1055/s-2008-1078636
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereocontrolled Thermal Pericyclic Cascade Rearrangement
S. E. Steinhardt, J. S. Silverston, C. D. Vanderwal*
University of California at Irvine, USA
Further Information
Publication History
Publication Date:
22 August 2008 (online)
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.