Document Detail


Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones.
MedLine Citation:
PMID:  15987209     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[reaction: see text] Highly regioselective, catalytic asymmetric reductive coupling reactions of 1,3-enynes and ketones have been achieved using catalytic amounts of Ni(cod)(2) and a P-chiral, monodentate ferrocenyl phosphine ligand. These couplings represent the first examples of catalytic, intermolecular reductive coupling of alkynes and ketones, enantioselective or otherwise, and afford synthetically useful 1,3-dienes possessing a quaternary carbinol stereogenic center in up to 70% ee.
Authors:
Karen M Miller; Timothy F Jamison
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; 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:  7     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2005 Jul 
Date Detail:
Created Date:  2005-06-30     Completed Date:  2006-04-26     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3077-80     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, USA.
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MeSH Terms
Descriptor/Qualifier:
Alkynes / chemical synthesis*,  chemistry
Catalysis
Combinatorial Chemistry Techniques*
Indicators and Reagents
Ketones / chemical synthesis*,  chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Grant Support
ID/Acronym/Agency:
1S10RR13886-01/RR/NCRR NIH HHS; GM-063755/GM/NIGMS NIH HHS; GM-072566/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Alkynes; 0/Indicators and Reagents; 0/Ketones

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