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Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-14 00:00:00 , DOI: 10.1021/acs.orglett.7b03609
Bo Sun 1 , Roman Pluta 1 , Naoya Kumagai 1 , Masakatsu Shibasaki 1
Affiliation  

A direct catalytic Mannich-type reaction of α-oxygen-functionalized amides was achieved. The use of 7-azaindoline amide was crucial to facilitate direct enolization and subsequent stereoselective addition to imines in a cooperative catalytic system comprising a soft Lewis acid and Brønsted base. The operationally simple room-temperature protocol furnished a syn-Mannich adduct with high stereoselectivity. Divergent functional group transformation of the amide moiety of the product allowed for expeditious access to enantioenriched syn-configured α-hydroxy-β-amino carboxylic acid derivatives, highlighting the synthetic utility of the present catalysis.

中文翻译:

直接催化不对称曼尼希型反应生成α-羟基-β-氨基酸衍生物

实现了α-氧官能化酰胺的直接催化曼尼希型反应。在含有软路易斯酸和布朗斯台德碱的协同催化体系中,使用7-氮杂吲哚啉酰胺对于促进直接烯胺化和随后向亚胺的立体选择性加成至关重要。该操作简单的室温方案提供了具有高立体选择性的曼尼希加合物。产物酰胺部分的不同官能团转化使得可以迅速获得对映体富集的顺式α-羟基-β-氨基羧酸衍生物,从而突出了本发明催化剂的合成用途。
更新日期:2018-01-14
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