Pentanidium–Catalyzed Enantioselective α‑Hydroxylation of Oxindoles Using Molecular Oxygen

Pentanidium-catalyzed α-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. Th...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 14; no. 18; pp. 4762 - 4765
Main Authors Yang, Yuanyong, Moinodeen, Farhana, Chin, Willy, Ma, Ting, Jiang, Zhiyong, Tan, Choon-Hong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.09.2012
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Hydroxylation
Indoles - chemistry
Molecular Structure
Oxygen - chemistry
Phosphites - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
QUATERNARY AMMONIUM-IONS
OXIDATION
KETONES
ASYMMETRIC-SYNTHESIS
KINETIC RESOLUTION
ESTERS
PHASE-TRANSFER CATALYSTS
Online AccessGet full text

Cover

More Information
Summary:Pentanidium-catalyzed α-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxide oxindole via reduction with enolates generated from the oxindoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302030v