Document Detail


Silyl Imine Electrophiles in Enantioselective Catalysis: A Rosetta Stone for Peptide Homologation, Enabling Diverse N-Protected Aryl Glycines from Aldehydes in Three Steps.
MedLine Citation:
PMID:  24828455     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
We report that N-(trimethylsilyl)imines serve in the Bis(AMidine)-catalyzed addition of bromonitromethane with a high degree of enantioselection. This allows for the production of a range of protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung Amide Synthesis (UmAS). Hence, peptide homologation with nonnatural aryl glycine amino acids is achieved in three steps from aromatic aldehydes, which are plentiful and inexpensive. Epimerization during the homologation step is circumvented by avoiding an α-amino acid intermediate.
Authors:
Dawn M Makley; Jeffrey N Johnston
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-5-14
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2014 May 
Date Detail:
Created Date:  2014-5-15     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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