Enantioselective organocatalytic formal [3+3]-cycloaddition of α,β-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol
Enantioselective organocatalytic formal [3+3]-cycloaddition of α,β-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol
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DOI：
10.1021/ol060486
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发表时间：
2006-05-25
期刊：
影响因子：
5.2
通讯作者：
Liao, Ju-Hsiou
中科院分区：
文献类型：
--
作者：
Hong, Bor-Cherng;Wu, Ming-Fun;Liao, Ju-Hsiou
首次报道了α，β-不饱和醛的高对映选择性有机催化碳[3 + 3]级联环加成反应。使用这种方法，巴豆醛被转化为6-羟基-4-甲基环己-1-烯甲醛，其用于合成（-）-异蒲勒醇水合物、（-）-山苍子醇和对甲苯甲醛以及（-）-6-羟基-4-甲基-1-环己烯-1-甲醇乙酸酯，其是石松属生物碱麦哲伦的全合成中的中间体。其他α，β-不饱和醛通过形式[4 + 2]反应产生手性环己二烯。
The first highly enantioselective organocatalyzed carbo [3 + 3] cascade cycloaddition of alpha,beta-unsaturated aldehydes is reported. Using this methodology, crotonaldehyde is converted to 6-hydroxy-4-methylcyclohex-1-enecarbaldehyde, which is used in the synthesis of (-)-isopulegol hydrate, (-)-cubebaol, and p-tolualdehyde as well as (-)-6-hydroxy-4-methyl-1-cyclohexene-1-methanol acetate, an intermediate in the total synthesis of lycopodium alkaloid magellanine. Other alpha,beta-unsaturated aldehydes give rise to chiral cyclohexadienes via formal [4 + 2] reactions.