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Synfacts 2008(5): 0511-0511  
DOI: 10.1055/s-2008-1072671
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Solvent-Dependent Chemodivergent Synthesis of Cyclic Ethers

Contributor(s): Mark Lautens, Frédéric Ménard
S.-H. Kim, S.-J. Oh, P.-S. Ho, S.-C. Kang, K.-J. O, C.-M. Yu*
Sungkyunkwan University, Suwon, Korea
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

A simple change of solvent leads to either five- or seven-membered oxacycles by what are proposed to be completely different mechanisms. Both tetrahydrofurans 3 and tetra­hydrooxepines 4 were obtained selectively as the cis-disubstituted isomers. The vinylstannane moiety of trisubstituted THFs 3 was shown to be easily derivatized to a range of functional groups (6).