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Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ2‐Pyrrolin‐4‐ones to Isatin Imines
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-01-15 , DOI: 10.1002/adsc.201701384
Sebastijan Ričko 1 , Anže Meden 1 , Luka Ciber 1 , Bogdan Štefane 1 , Franc Požgan 1 , Jurij Svete 1 , Uroš Grošelj 1
Affiliation  

Racemic Δ2‐pyrrolin‐4‐ones (i. e. 4‐pyrrolones), easily available in two steps from N‐protected α‐amino acids, undergo organocatalysed asymmetric Mannich‐type addition to isatin‐derived ketimines to furnish the non‐racemic oxindole‐Δ2‐pyrrolin‐4‐one adducts, stereoselectively (up to 96% ee, dr≥15:1). The oxindole–pyrrolone products feature vicinal tetrasubstituted carbon stereocenters. The developed protocol has a broad substrate scope and tolerates diverse substituents at position C‐5 in 4‐pyrrolones and at positions N‐1 and C‐5/7 in isatin imines.

中文翻译:

通过Mannich型有机催化将Δ2-吡咯啉-4-酮加到Isatin亚胺上来构建四联取代的立体立体中心

外消旋Δ 2 -吡咯啉-4-酮(4-吡咯酮类)中,从两个步骤容易获得ñ -保护的α -氨基酸,离岗organocatalysed不对称曼尼希型除靛红衍生的酮亚胺,得到非外消旋的羟吲哚-Δ 2 -吡咯啉-4-酮加合物,立体选择性(高达96%ee值博士≥15:1)。羟吲哚-吡咯烷酮产品具有邻近的四取代碳立体中心。所开发的方案具有广泛的底物范围,并且可以耐受4-吡咯烷酮中C-5位置以及异亚胺中N-1和C-5 / 7位置的各种取代基。
更新日期:2018-01-15
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