Document Detail


Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines.
MedLine Citation:
PMID:  12762658     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[reaction: see text] A useful method for the conversion of prochiral allylic alcohols to chiral allylic amines of high enantiopurity is reported. N-(4-Methoxyphenyl)trifluoroacetimidates are excellent substrates for the palladium(II)-catalyzed allylic imidate rearrangement as the allylic trifluoroacetamide products can be deprotected in two steps to provide chiral nonracemic allylic amines. Di-mu-chlorobis[(eta(5)-(S)-(pR)-2-(2'-(4'-isopropyl))oxazolinylcyclopentadienyl,1-C,3'-N))(eta(4)-tetraphenylcyclobutadiene)cobalt]dipalladium (6a, COP-Cl) is a superior catalyst because it does not require activation with silver salts and provides rearranged allylic trifluoroacetamides in good yields and high enantiomeric purities.
Authors:
Larry E Overman; Carolyn E Owen; Mary M Pavan; Christopher J Richards
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.; 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 May 
Date Detail:
Created Date:  2003-05-23     Completed Date:  2003-09-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1809-12     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, California 92697-2025, USA. leoverma@uci.edu
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MeSH Terms
Descriptor/Qualifier:
Alcohols / chemical synthesis,  chemistry
Allyl Compounds / chemical synthesis*,  chemistry
Amines / chemical synthesis,  chemistry
Catalysis
Imidoesters / chemical synthesis*,  chemistry
Indicators and Reagents
Silver / chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Alcohols; 0/Allyl Compounds; 0/Amines; 0/Imidoesters; 0/Indicators and Reagents; 7440-22-4/Silver

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


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