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Synfacts 2010(6): 0710-0710
DOI: 10.1055/s-0029-1219998
DOI: 10.1055/s-0029-1219998
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Synthesis of Bicyclo[2.2.2]oct-5-en-2-one by Using Organocatalysis
N. Holub, H. Jiang, M. W. Paixão, C. Tiberi, K. A. Jørgensen*
Aarhus University, Denmark
Further Information
Publication History
Publication Date:
20 May 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201006/lookinside/thumbnails/10.1055-s-0029-1219998-1.jpg)
Significance
Jørgensen and co-workers report an unexpected Michael-aldol-Smiles rearrangement sequence for the preparation of 6-substituted bicyclo[2.2.2]oct-5-ene-2-ones 4 with high enantioselectivity. The corresponding Michael adducts 3 of cyclohexenone and β-keto benzothiazoyl sulfones 1 can be easily cyclized under mild reaction conditions. The authors also performed various transformations on the obtained bicyclic compounds, such as ring-expanding Baeyer-Villiger oxidation, Schmidt reaction and rearrangement reactions.