A Lewis Acid Promoted Oxidative Cyclization

Replacing trifluoroacetic acid with a catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little as 0.2 mol %. Furthermore, these mildly aci...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 74; no. 16; pp. 6394 - 6397
Main Authors Donohoe, Timothy J, Winship, Paul C. M, Walter, Daryl S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2009
Amer Chemical Soc
Subjects
Acids - chemistry
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Osmium - chemistry
Oxidation-Reduction
Physical Sciences
Preparations and properties
Reactivity and mechanisms
Science & Technology
OSMIUM
Lewis acid
Protecting group
Catalytic reaction
Nitrogen heterocycle
Furan derivatives
Transition metal
Oxygen heterocycle
Osmium compound
Pyrrolidine derivatives
Chemical reduction
Cyclization
Oxidation
Platinoid
Acid medium
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Summary:Replacing trifluoroacetic acid with a catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little as 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901243y