A novel tandem [2+2] cycloaddition-Dieckmann condensation with ynolate anions.: Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n+1] cycloaddition
A novel tandem [2+2] cycloaddition-Dieckmann condensation with ynolate anions.: Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n+1] cycloaddition
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DOI：
10.1021/jo015929w
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发表时间：
2001-11-16
影响因子：
3.6
通讯作者：
Shishido, K
中科院分区：
文献类型：
--
作者：
Shindo, M;Sato, Y;Shishido, K
描述了一种新型的通过壬酯阴离子的串联[2 + 2]环加成-迪克曼缩合反应。通过不涉及相应β -内酯烯醇化的途径，Ynolate阴离子对于形成活性β -内酯烯醇化是有用的。[2 + 2]羰基阴离子与-或-酮酯进行环加成，然后进行Dieckmann缩合，得到双环-内酯，这些内酯很容易脱羧，在一个锅中产生合成上有用的2,3-二取代环戊烯酮和环己烯酮。这种串联反应被应用于一种新的、一锅合成高取代萘的方法。
A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive beta -lactone enolates via a pathway not involving the enolization of the corresponding beta -lactones. The [2 + 2] cycloaddition of ynolate anions with delta- or gamma -keto esters, followed by Dieckmann condensation, gives bicyclic beta -lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.