Photocyclization reactions of epoxy nitriles via carbonyl ylides. Formation of spiroketals, spiroethers, and a spirolactone

DOI: 10.1248/cpb.43.1621

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1621 - 1628 (1995)

Update date:2022-09-26

Topics:

Authors:

Kotera Kotera

Ishii Ishii

Sakamoto

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Article abstract of DOI:10.1248/cpb.43.1621

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

Full text of DOI:10.1248/cpb.43.1621

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