The reductive aldol reaction of electron deficient aromatic compounds has been investigated and found to be a viable method for carbon-carbon bond formation. Reductions under ammonia and ammonia-free conditions were both capable of facilitating the aldol reaction although the latter showed more scope for reaction with enolisable aldehydes. Moreover, reduction under ammonia-free conditions allowed the addition of Lewis acids which improved stereoselectivity to favour the anti stereoisomer. Production of the syn diastereoisomer was possible through either one of two different protocols performed after partial reduction was complete. While the main emphasis of this paper concerns the reductive aldol reaction of electron deficient pyrroles, it was also shown that both benzenoid and furan aromatic compounds were amenable to such reducing conditions.

中文翻译：

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还原性醛醇缩合反应的范围：适用于芳族碳环和杂环。

已经研究了缺电子的芳族化合物的还原性醛醇缩合反应，并且发现其是形成碳-碳键的可行方法。在氨水和无氨条件下的还原都能够促进醛醇缩合反应，尽管后者显示出与可缩醛的反应空间更大。此外，在无氨条件下的还原允许添加路易斯酸，该路易斯酸改善了立体选择性，从而有利于抗立体异构体。通过部分还原完成后进行的两种不同操作中的一种，可以生产顺式非对映异构体。尽管本文的主要重点是缺乏电子的吡咯的还原性醛醇缩合反应，但还表明，苯并类和呋喃芳族化合物都适合这种还原条件。