Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH) CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, Spain.
Molecules. 2018 Oct 19;23(10):2692. doi: 10.3390/molecules23102692.
Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of β-isocupreidine catalyst are reported. The moderate, but promising, enantioselectivity observed (40⁻54% ee), opens the door to a new area of research for the asymmetric construction of new chiral 1,4-dihydropyridine derivatives, whose enantioselective catalytic preparation are still very limited. Moreover, the use of hydrazones for the enantioselective construction of chiral 1,4-dihydropyridines has been overlooked in the literature so far. Therefore, our research represents a pivotal example in this field which remains still unexplored.
初步研究结果表明,在β-异芦竹碱催化剂的存在下,通过腙与亚甲基丙二腈的反应,可实现高官能化 1-苯甲酰胺基-1,4-二氢吡啶衍生物的不对称合成。观察到的中等但有前途的对映选择性(40⁻54%ee)为不对称构建新型手性 1,4-二氢吡啶衍生物开辟了新的研究领域,而这些衍生物的对映选择性催化制备仍然非常有限。此外,目前文献中尚未报道使用腙来对映选择性构建手性 1,4-二氢吡啶。因此,我们的研究代表了该领域中一个重要的范例,该领域仍有待探索。