The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde
The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde
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DOI：
10.1016/j.tetlet.2009.02.091
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发表时间：
2009-07-01
影响因子：
1.8
通讯作者：
Jun, Chul-Ho
中科院分区：
文献类型：
--
作者：
Jo, Eun-Ae;Jun, Chul-Ho
以环己胺、对三氟甲基苯甲酸、威尔金森络合物和2-氨基-3-甲基吡啶为催化剂，实现了1-烯烃与脂肪醛的分子间氢酰化反应。通过将环己胺共轭加成到最初产生的羟醛中间体上，然后对所得β-氨基醛亚胺进行逆曼尼希型断裂，避免了不需要的羟醛副产物的形成。
Efficient intermolecular hydroacylation of 1-alkene with aliphatic aldehyde was achieved using a catalyst mixture of cyclohexylamine, p-trifluoromethylbenzoic acid, Wilkinson's complex and 2-amino-3-picoline. The formation of unwanted aldol side-product was avoided through the conjugate addition of cyclohexylamine to the aldol intermediate that was initially generated, followed by the retro-Mannich-type fragmentation of the resulting beta-aminoaldimine.