Document Detail


5,5-Dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups.
MedLine Citation:
PMID:  12098295     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.
Authors:
Michel Couturier; John L Tucker; Caroline Proulx; Ghislain Boucher; Pascal Dubé; Brian M Andresen; Arun Ghosh
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Jul 
Date Detail:
Created Date:  2002-07-05     Completed Date:  2003-01-16     Revised Date:  2003-11-03    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4833-8     Citation Subset:  -    
Affiliation:
Process Research and Development, Pfizer Global Research and Development, Eastern Point Road, P.O. Box 8013, Groton, Connecticut 06340-8013, USA. michael_a_couturier@groton.pfizer.com
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