Organocatalytic Asymmetric Mannich Reaction of 3‑Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated N‑Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole–Diamines/Amino Alcohols

A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally...

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Published inJournal of organic chemistry Vol. 81; no. 13; pp. 5270 - 5277
Main Authors Shan, Jing, Cui, Baodong, Wang, Yu, Yang, Chengli, Zhou, Xiaojian, Han, Wenyong, Chen, Yongzheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA-AMINATION
TMC-95A
HYDROXYLATION
CONSTRUCTION
3-AMINOOXINDOLES
BEARING
INHIBITORS
EFFICIENT
3-HYDROXY-2-OXINDOLES
CATALYSTS
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Summary:A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally diverse vicinal oxindole–diamines/amino alcohols were smoothly obtained in moderate to high yields (up to 99%) with good to excellent diastereoselectivities and enantioselectivities (up to 95:5 dr and 96% ee). The synthetic application of this protocol was also demonstrated by the versatile transformation of chiral vicinal oxindole–diamine/amino alcohol into spirocyclic oxindoles.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00278