Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines

A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral i...

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Published inJournal of the American Chemical Society Vol. 135; no. 9; pp. 3343 - 3346
Main Authors Liu, Guan-Sai, Zhang, Yong-Qiang, Yuan, Yong-An, Xu, Hao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2013
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Ferrous Compounds - chemistry
Hydroxylamine - chemical synthesis
Hydroxylamine - chemistry
Hydroxylation
Molecular Structure
Physical Sciences
Science & Technology
UNFUNCTIONALIZED OLEFINS
ORGANIC-SYNTHESIS
ENANTIOSELECTIVE AZIRIDINATION
COUPLING REACTIONS
ALKENE AZIRIDINATION
MECHANISTIC INSIGHT
TETHERED AMINOHYDROXYLATION
IRON
CATALYZED ASYMMETRIC EPOXIDATION
C-H AMINATION
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Summary:A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja311923z