New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes. The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary. The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for 7 days at 80°C, affording a good yield of the amino alcohols. Except for styrene oxide which gave both α- and β-amino alcohols, the reactions led regioselectively to the corresponding diastereomeric β-amino alcohols. The resulting diastereomers were separated, and the configurations of their stereogenic centers were established. The obtained enantiomerically pure 2-pyridinyl- and 6-(2,2′-bipyridinyl)-β-amino alcohols were tentatively tested as chiral ligands in the zinc-catalyzed aldol reaction.

中文翻译：

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2-环氧乙烷基吡啶：手性胺的合成和区域选择性环氧化物开环作为手性配体的途径

从各自的α-甲基氮杂芳烃合成了新的环氧化物、吡啶衍生物、2,2'-联吡啶和1,10-菲咯啉。获得的外消旋 2-环氧乙烷基-氮杂芳烃与氧化苯乙烯和反式-二苯乙烯氧化物一起以手性伯胺作为手性助剂进行开环。最有效的反应是在 Sc(OTf)3/二异丙基乙胺的存在下，在 80°C 下进行 7 天，得到良好的氨基醇收率。除了产生α-和β-氨基醇的氧化苯乙烯外，反应区域选择性地导致相应的非对映体β-氨基醇。分离得到的非对映异构体，并确定其立体中心的构型。得到的对映体纯的 2-吡啶基-和 6-(2,