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): 0987-0987
DOI: 10.1055/s-2008-1078674
DOI: 10.1055/s-2008-1078674
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Organocatalytic Asymmetric Claisen Rearrangement
C. Uyeda, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Significance
Catalysis of the Claisen rearrangement by simple guanidinium salts such as N,N′-diphenylguanidinium salt 1 is reported. A broad variety of substituted allyl vinyl ethers (see selected examples) were suitable substrates for this interesting transformation. Moreover, highly enantioselective Claisen rearrangements of ester-substituted allyl vinyl ethers 2 have been achieved using C 2-symmetric guanidinium salt 3 as the catalyst. Other types of substrates failed to give satisfying results in the asymmetric variant. The weakly coordinating counterion BArF- was found to be crucial for catalytic activity of the respective guanidinium salt.