Document Detail


Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)(3).
MedLine Citation:
PMID:  11749624     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Bi(OTf)(3)-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)(3)/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable methyl ester realized quite easy separation of the desired acylation product. The Bi(OTf)(3)/acid anhydride protocol was applicable to a wide spectrum of alcohols bearing various functionalities. Acid-labile THP- or TBS-protected alcohol, furfuryl alcohol, and geraniol could be acylated as well as base-labile alcohols. Even acylation of functionalized tertiary alcohols was effected at room temperature.
Authors:
A Orita; C Tanahashi; A Kakuda; J Otera
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  66     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2001 Dec 
Date Detail:
Created Date:  2001-12-25     Completed Date:  2002-02-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8926-34     Citation Subset:  IM    
Affiliation:
Okayama University of Science, 1-1 Ridai-Cho, Okayama 700-0005, Japan.
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MeSH Terms
Descriptor/Qualifier:
Acylation
Alcohols / chemistry*
Carbohydrates / chemistry
Catalysis
Magnetic Resonance Spectroscopy
Mesylates*
Nucleosides / chemistry
Chemical
Reg. No./Substance:
0/Alcohols; 0/Bi(OTf)3; 0/Carbohydrates; 0/Mesylates; 0/Nucleosides

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