Synthesis of 4--2-hydroxybutanolides and (Z)-4-Alkylidene-2-butenolides through Cycloadditions Using a Phosphorus-Functionalized Nitrile Oxide

DOI: 10.1246/bcsj.62.171

Source and publish data:

Bulletin of the Chemical Society of Japan p. 171 - 179 (1989)

Update date:2022-08-12

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Authors:

Kanemasa, Shuji

Nakagawa, Norihiko

Suga, Hiroyuki

Tsuge, Otohiko

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Article abstract of DOI:10.1246/bcsj.62.171

A sequence of cycloadditions of (diethoxyphosphinyl)acetonitrile oxide with α,β-unsaturated esters, the Raney Ni reduction of the resulting cycloadducts, the Horner-Emmons olefination, and the carbonyl reduction with sodium borohydride leads to 5-<(E)-1-alkenyl>-3-hydroxy-4,5-dihydro-2(3H)-furanones which can be converted into (Z)-5-alkylidene-2(5H)-furanones in two steps.

Full text of DOI:10.1246/bcsj.62.171

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