有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
ロジウム錯体触媒による4-アルキナールの分子内ヒドロアシル化反応
田中 健
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ジャーナル フリー

2005 年 63 巻 4 号 p. 351-358

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A novel intramolecular trans-hydroacylation of 4-alkynals leading to cyclopentenones was accomplished by using a cationic rhodium (I) complex. We also developed three types of new reactions, 1) reaction of 4-alkynals with phenol to provide cis-4-alkenoates, 2) [4 + 2] cycloaddition of 4-alkynals with alkynes to provide cyclohexenones, and 3) isomerization of 4-alkynals to 1, 3-dienals, through five-membered rhodium metallacycles generated from 4-alkynals. The asymmetric variants of this intramolecular hydroacylation reaction were successfully developed by using 3-methoxy-4-alkynals as the substrates. The present method represents an attractive new route to highly functionalized cyclopentenones and cyclobutanones.

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