Document Detail


Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.
MedLine Citation:
PMID:  21785516     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets.
Authors:
Bhaskar C Das; Seetaram Mohapatra; Philip D Campbell; Sabita Nayak; Sakkarapalayam M Mahalingam; Todd Evans
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Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  Tetrahedron letters     Volume:  51     ISSN:  0040-4039     ISO Abbreviation:  -     Publication Date:  2010 May 
Date Detail:
Created Date:  2011-7-25     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2984819R     Medline TA:  Tetrahedron Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  2567-2570     Citation Subset:  -    
Affiliation:
Department of Nuclear Medicine, Albert Einstein College of Medicine, Bronx, NY 10461, USA.
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MeSH Terms
Descriptor/Qualifier:
Grant Support
ID/Acronym/Agency:
R37 HL056182-15//NHLBI NIH HHS

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