Photocyclization Reactions of Epoxy Nitriles via Carbonyl Ylides. Formation of Spiroketals, Spiroethers, and a Spirolactone

Masashi KOTERA; Keitaro ISHII; Masanori SAKAMOTO

doi:10.1248/cpb.43.1621

Masashi KOTERA, Keitaro ISHII, Masanori SAKAMOTO

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Keywords: carbonyl ylide, epoxy nitrile, spiroketal, photochemistry, anomeric effect, diastereoselectivity

JOURNAL FREE ACCESS

1995 Volume 43 Issue 10 Pages 1621-1628

DOI https://doi.org/10.1248/cpb.43.1621

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Abstract

Photocyclization reactions (γ=254nm) of γ-methyl δ-(4-hydroxybutyl) and δ-(-4-hydroxypentyl) α, β-unsaturated γ, δ-epoxy nitriles gave spiroketals and spirothers diastereoselectively, whereas reaction of δ-(6-hydroxyhexyl) nitrile allorded no cyclization product. In addition, photocyclization of nitrile bearing a carboxyl group in the δ-side-chain afforded spirolactone.

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