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Solvent-Minimized, Chromatography-Free, Diastereoselective Synthesis of Oxazolidine-Dispirooxindoles via oxa-1,3-Dipolar Cycloaddition of 3-Oxindole.

Authors :
Peng-Ju Xia
Jun Li
Yu-Lun Qian
Qing-Lan Zhao
Hao-Yue Xiang
Jun-An Xiao
Xiao-Qing Chen
Hua Yang
Source :
Journal of Organic Chemistry. 3/2/2018, Vol. 83 Issue 5, p2948-2953. 6p.
Publication Year :
2018

Abstract

An efficient and diastereoselective decarboxylative oxa-1,3-dipolar cycloaddition between 3-oxindoles and diverse amino acids is developed to access novel oxazolidine-dispirooxindole skeletons bearing vicinal quaternary carbon centers. This protocol features operational simplicity, a broad substrate scope, and good to excellent chemical yields and diastereoselectivities. In particular, minimal solvent (1 mL/10 mmol) and chromatography-free purification render this synthetic process more efficient and environmentally benign in the context of green chemistry. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
83
Issue :
5
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
128354887
Full Text :
https://doi.org/10.1021/acs.joc.7b02865