Document Detail


Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids.
MedLine Citation:
PMID:  22991924     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO(2) caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.
Authors:
Masatoshi Shibuya; Ryu̅suke Doi; Takuro Shibuta; Shun-Ichiro Uesugi; Yoshiharu Iwabuchi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-19
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-20     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3 Aobayama, Sendai 980-8578, Japan.
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