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Synfacts 2007(12): 1269-1269
DOI: 10.1055/s-2007-991343
DOI: 10.1055/s-2007-991343
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Transannular Diels-Alder Reaction Catalyzed by Chiral Oxazaborolidine
E. P. Balskus, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information
Publication History
Publication Date:
22 November 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200712/lookinside/thumbnails/10.1055-s-2007-991343-1.jpg)
Significance
While catalytic, asymmetric intermolecular and intramolecular Diels-Alder reactions are well established, the present paper provides the first report of the corresponding transannular Diels-Alder (TADA) reaction. A survey of various Lewis and Brønsted acid catalysts revealed that oxazaborolidine 1 was the only catalyst able to promote cyclization of macrolactone 2 (n, m = 1). Subsequently, various-sized macrocycles containing α,β-unsaturated lactone or ketone dienophilic moieties were cyclized to furnish tricyclic endo products containing medium-to-large-sized rings in good to excellent diastereo- and enantioselectivities.