Document Detail

Enantioselective alpha-silyl amino acid synthesis by reverse-aza-Brook rearrangement.
MedLine Citation:
PMID:  14627413     Owner:  NLM     Status:  MEDLINE    
[reaction: see text] Asymmetric reverse-aza-Brook rearrangement of N-Boc-N-trialkylsilyl allylamine yields an enantiomerically enriched alpha-amino allylsilane. Oxidative cleavage of the alkene leads to a Boc-protected amino acid with the configuration of naturally occurring amino acids (L). Standard coupling protocols, including the use of trifluoroacetic acid for removal of the Boc group, yield a tripeptide with a central silane amino acid.
Guodong Liu; Scott McN Sieburth
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  5     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2003 Nov 
Date Detail:
Created Date:  2003-11-20     Completed Date:  2004-05-24     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4677-9     Citation Subset:  IM    
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
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MeSH Terms
Allylamine / chemistry
Amino Acids / chemical synthesis*,  chemistry*
Molecular Structure
Peptides / chemical synthesis*,  chemistry
Silanes / chemistry*
Trifluoroacetic Acid / chemistry
Reg. No./Substance:
0/Amino Acids; 0/Peptides; 0/Silanes; 107-11-9/Allylamine; 76-05-1/Trifluoroacetic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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