Synfacts 2011(2): 0215-0215  
DOI: 10.1055/s-0030-1259348
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Guanidinium-Catalyzed Enantioselective Claisen Rearrangement

Contributor(s): Benjamin List, Steffen Müller
C. Uyeda, A. R. Rötheli, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information

Publication History

Publication Date:
19 January 2011 (online)

Significance

Jacobsen and co-workers disclose the enantioselective Claisen rearrangement of O-allyl β-keto esters catalyzed by chiral guanidinium salt 1. The desired products were obtained with good yields and enantioselectivities from a broad variety of different substrates, including substituted O-allyl β-keto esters leading to the ­formation of vicinal stereocenters. The utility of the products was demonstrated in the enantio­selective construction of the hyperforin core structure. Furthermore, the recyclability of the catalyst was demonstrated, and computational studies modeling the reaction pathway and a plausible transition state are provided.