Reagent design and study of allene as a promising class of reagents (synthons) for cycloaddition. The site-selective and regioselective Diels-Alder reactions of ( …

…, H Nishiyama, K Kanematsu

Index: Hayakawa, Kenji; Nishiyama, Hitoshi; Kanematsu, Ken Journal of Organic Chemistry, 1985 , vol. 50, # 4 p. 512 - 517

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Citation Number: 83

Abstract

We also examined the Diels-Alder reactions of 1 with acyclic silyl enol ethers 6-8 (Table I). The reaction of 1 with 1-(trimethylsi1oxy) buta-l, &diene (6) at 160" C (sealed tube, 8 h) followed by a rapid chromatography on a small amount of silica gel afforded the adduct 13a in 72% yield. When the reaction mixture was treated with acetic acid prior to chromatography, the alcohol 13b was obtained in 75% yield as a sole product. In the ...