Diastereoselective Aldol and Reformatsky Reactions of α-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride

Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester wit...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2000-11, Vol.73 (11), p.2579-2585
Main Authors: Kagayama, Akifumi, Igarashi, Koji, Shiina, Isamu, Mukaiyama, Teruaki
Format: Article
Language:English
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Summary:Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.73.2579