Platinum(II) Salt Catalyzed Annulation of Hydroxyalkyl-Substituted ­Vinylsilanes with Aldehydes

Katsukiyo Miura; Ryo Itaya; Makoto Horiike; Hiroyuki Izumi; Akira Hosomi

doi:10.1055/s-2005-921926

LETTER

Platinum(II) Salt Catalyzed Annulation of Hydroxyalkyl-Substituted Vinylsilanes with Aldehydes

Katsukiyo Miura*^a, Ryo Itaya^a, Makoto Horiike^a, Hiroyuki Izumi^a, Akira Hosomi*^a,b
^a Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, and CREST, Japan Science and Technology Corporation (JST), Tsukuba, Ibaraki 305-8571, Japan
Fax: +81(29)8536503; e-Mail: miura@chem.tsukuba.ac.jp; e-Mail: hosomi@chem.tsukuba.ac.jp;
^b Faculty of University Evaluation and Research, National Institution for Academic Degrees and University Evaluation, Kodaira, Tokyo 187-8587, Japan

Abstract

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Abstract

In the presence of catalytic amounts of PtCl₂ and AgX (X = OTf or SbF₆), (Z)-6-trimethylsilyl-5-hexen-1-ol and (Z)-5-trimethylsilyl-4-penten-1-ol reacted smoothly with aldehydes to give 2,3-disubstituted tetrahydropyrans and tetrahydrofurans, respectively, in good to high yields. The reaction mechanism involves the isomerization of the starting vinylsilanes to the corresponding allylsilanes and subsequence Prins-type annulation with aldehydes.

Key words

aldehydes - annulations - catalysis - silicon - tandem reactions

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References

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Platinum(II) Salt Catalyzed Annulation of Hydroxyalkyl-Substituted ­Vinylsilanes with Aldehydes

Platinum(II) Salt Catalyzed Annulation of Hydroxyalkyl-Substituted Vinylsilanes with Aldehydes