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首页> 外文期刊>Chemistry: A European journal >The zirconium alkoxide-catalyzed aldol-Tishchenko reaction of ketone aldols
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The zirconium alkoxide-catalyzed aldol-Tishchenko reaction of ketone aldols

机译：酮醇醛的锆醇盐锆催化的Aldol-Tishchenko反应

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摘要

The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.
机译：酮醇作为烯醇当量的醇醛-季申科反应已被开发为一种有效的策略，可一步完成差异化的1,3-抗二醇单酯。热力学不稳定的酮醛醇醛容易地逆醛醇缩合，原位产生推测的烯醇锆，然后通常以高收率和完全的1,3-抗非对映体进行醛醇-季申科反应。对各种金属醇盐作为催化剂的评估和对反应方案的优化导致了一种路易斯酸度降低和二氯甲烷作为溶剂的改性醇锆氧化物催化剂，从而在很大程度上抑制了不希望的酰基迁移。已经制备了各种酮醛醇缩醛，并对其进行了常规方法，产生了范围广泛的不同取代的1，3-抗二醇单酯，它们可以水解为相应的1，3-抗二醇。

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