Document Detail


Highly selective reaction of alpha-halo-alpha,beta-unsaturated esters with ketones or aldehydes promoted by SmI2: an efficient alternative access to Baylis-Hillman adducts.
MedLine Citation:
PMID:  15932309     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
A samarium diiodide promoted addition of aromatic or aliphatic beta-substituted-alpha-halo-alpha,beta-unsaturated esters 1 or 3 to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates 2 and 4 in good yields and very high stereoselectivity. This method constitutes an efficient and valuable alternative to the synthesis of Baylis-Hillman adducts. A mechanism is proposed to explain this transformation.
Authors:
José M Concellón; Mónica Huerta
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Jun 
Date Detail:
Created Date:  2005-06-03     Completed Date:  2005-07-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4714-9     Citation Subset:  -    
Affiliation:
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, C. Julián Clavería 8, 33071 Oviedo, Spain. jmcg@fq.uniovi.es
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