Boron Tribromide-Assisted Chiral Phosphoric Acid Catalyst for a Highly Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines
Boron Tribromide-Assisted Chiral Phosphoric Acid Catalyst for a Highly Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines
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DOI：
10.1021/jacs.5b08693
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发表时间：
2015-10-28
影响因子：
15
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Hatano, Manabu;Goto, Yuta;Ishihara, Kazuaki
BBr3-手性磷酸配合物是高效实用的路易斯酸辅助布朗斯台德酸（LBA）催化剂，用于促进α-取代丙烯醛和α-CF3丙烯酸酯的对映选择性狄尔斯-阿尔德（DA）反应。特别是，α-取代的丙烯醛与1,2-二氢吡啶的DA反应得到了具有高对映选择性的相应光学活性异奎宁环。此外，还证明了向吲哚生物碱、长春质和别长春质的关键中间体的转化。
BBr3-chiral phosphoric acid complexes are highly effective and practical Lewis acid-assisted Bronsted acid (LBA) catalysts for promoting the enantioselective Diels-Alder (DA) reaction of a-substituted acroleins and alpha-CF3 acrylate. In particular, the DA reaction of alpha-substituted acroleins with 1,2-dihydropyridines gave the corresponding optically active isoquinuclidines with high enantioselectivities. Moreover, transformations to the key intermediates of indole alkaloids, catharanthine and allocatharanthine, are demonstrated.