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Synfacts 2006(1): 0026-0026
DOI: 10.1055/s-2005-921693
DOI: 10.1055/s-2005-921693
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of Fused Tetrahydropyrans
N. Hiramatsu, N. Takahashi, R. Noyori, Y. Mori*
Meijo University, Nagoya, and Nagoya University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Dezember 2005 (online)
Significance
A radical-induced conjugate addition is used for the highly diastereoselective cyclization of acetylenic β-alkoxyacrylates to give tetrahydropyrans. The reaction proceeds rapidly using tributylstannane with AIBN as radical initiator. The facile protodestannylation of the products leads to fused tetrahydropyrans with reactive functionality for further manipulation.