Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N‑(4‑Toluenesulfonyloxy)carbamates

N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yield...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 77; no. 19; pp. 8480 - 8491
Main Authors Masruri, Willis, Anthony C, McLeod, Malcolm D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2012
Amer Chemical Soc
Subjects
Aliphatic compounds
Alkenes - chemistry
Amination
Carbamates - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Chemistry, Organic
Exact sciences and technology
General and physical chemistry
Glucosides - chemistry
Molecular Structure
Organic chemistry
Osmium - chemistry
Physical Sciences
Preparations and properties
Pyrimidinones - chemistry
Science & Technology
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
ALLYLIC ALCOHOL SYSTEMS
DIHYDROXYLATION
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
ASYMMETRIC AMINOHYDROXYLATION
AZIRIDINATION
EFFICIENT SYNTHESIS
OLEFINS
TETHERED AMINOHYDROXYLATION
C-H AMINATION
Protecting group
Catalytic reaction
Regioselectivity
Asymmetric molecule
Transition metal
Organic carbamate
Osmium
Alkene
Amine
Amination
Platinoid
Catalyst
Ethylenic compound
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Summary:N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301372y