A copper(I)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles

A Cu(I)/Ph-Phosferrox complex catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines has been described. This strategy can provide direct access to chiral 3-substituted 3-aminooxindoles bearing vicinal quaternary-tertiary carbon stereocenters in high yields (up t...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 1; pp. 70 - 74
Main Authors Zhu, Jing-Yan, Yang, Wu-Lin, Liu, Yang-Zi, Shang, Shao-Jing, Deng, Wei-Ping
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2018
Royal Society of Chemistry
Subjects
Chemical synthesis
Chemistry
Chemistry, Organic
Copper
Enantiomers
Glycine
Imines
Organic chemistry
Physical Sciences
Science & Technology
Substitutes
AZA-HENRY REACTION
OXINDOLES BEARING
COMPLEX
AMINO-ACIDS
IMINES
1,3-DIPOLAR CYCLOADDITION
CONSTRUCTION
BAYLIS-HILLMAN REACTION
AZOMETHINE YLIDES
DERIVATIVES
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Summary:A Cu(I)/Ph-Phosferrox complex catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines has been described. This strategy can provide direct access to chiral 3-substituted 3-aminooxindoles bearing vicinal quaternary-tertiary carbon stereocenters in high yields (up to 99%), excellent enantioselectivities (up to >99% ee) and moderate to high diastereoselectivities (up to 98 : 2 dr).
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c7qo00691h