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Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine.
Chemical & Pharmaceutical Bulletin ( IF 1.7 ) Pub Date : 2020-01-01 , DOI: 10.1248/cpb.c20-00130
Zhao Li 1 , Naoya Kumagai 1 , Masakatsu Shibasaki 1
Affiliation  

α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the In(III)/bishydroxamic acid complex. Although the enantioselectivity remains unsatisfactory, this work is an important step toward the development of an asymmetric catalysis utilizing stable and low-reactive substrates.

中文翻译:

α,β-不饱和酰胺和偶氮甲亚胺的催化不对称1,3-偶极环加成反应。

将α,β-不饱和酰胺以可行的偶极亲和性掺入偶氮甲亚胺的催化不对称1,3-偶极环加成中。使用7-氮杂吲哚啉助剂对于获得足够的反应性和出色的非对映选择性至关重要,这很可能是由于In(III)/双异羟肟酸络合物对酰胺的螯合活化作用。尽管对映选择性仍然不能令人满意,但这项工作是朝着利用稳定和低反应性底物发展不对称催化的重要一步。
更新日期:2020-01-01
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