Palladium-catalyzed asymmetric allylic alkylation of 3-amino-2-oxindoles: Synthesis of 3-allyl-3-amino-2-oxindoles

被引：4
|
作者：
Kumarswamyreddy, Nandarapu [1 ,2 ]
Jayakumar, Samydurai [1 ]
Kesavan, Venkitasamy [1 ]
机构：
[1] Indian Inst Technol Madras, Bhupat & Jyothi Metha Sch Biosci, Dept Biotechnol, Chem Biol Lab, Chennai 600036, Tamil Nadu, India
[2] Indian Inst Technol Tirupati, Dept Chem, Tirupati 517506, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2021年 / 82卷
关键词：
3-Ally-3-amino oxindoles; Asymmetric allylic alkylation; Palladium catalyst; Bi(oxazoline) ligands; Spiropyrrolidine oxindoles; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; MANNICH REACTION; QUATERNARY; ALLYLATION; OXINDOLES; ISATIN;
D O I：
10.1016/j.tetlet.2021.153385
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tartrate derived bi(oxazoline) ligand with palladium (II) species catalyzed asymmetric allylic alkylation reaction to access highly valuable 3-allyl-3-amino-2-oxindoles with vicinal quaternary and tertiary stereocenters in very good yields (up to 91%) and excellent enantioselectivity (up to 98% ee) with moderate to good diastereoselectivity (up to 5:1). The synthetic utility of 3-allyl-3-amino-2-oxindole was further demonstrated to construct spiro(oxindole-3,2'-pyrrolidine) with consecutive one quaternary and three tertiary chiral centers in good stereoselectivity (dr = 8:1 and 80% ee) through metal-free intramolecular iodocyclization reaction. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：6
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