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Synfacts 2008(1): 0077-0077  
DOI: 10.1055/s-2007-991442
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Indium-Catalyzed Cycloisomerization into Medium-Sized Rings

Contributor(s): Paul Knochel, Tobias Thaler
H. Tsuji, K.-i. Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura*
The University of Tokyo and Waseda University, Tokyo, Japan
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

The intramolecular Conia reaction was extended to the preparation of medium-sized and large (6- to 15-membered) rings. The reaction proceeds under moderately dilute conditions and the medium-sized rings are obtained even more readily than six-membered rings. This anomalous relationship between the ring size and the cyclization rate makes this reaction a powerful tool for the preparation of medium-sized to large rings, which are important scaffolds for natural products and odorants.