Electrotelluration:  A New Approach to Tri- and Tetrasubstituted Alkenes

A novel electrotelluration process is described in which a Michael addition of an alkyl or aryl tellurolate anion occurs onto an activated alkyne with subsequent trapping of a vinyl anion with electrophiles (aldehydes and ketones) other than a proton. This process provides an efficient regio- and st...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-09, Vol.67 (18), p.6291-6296
Main Authors: Marino, Joseph P, Nguyen, Hanh Nho
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:A novel electrotelluration process is described in which a Michael addition of an alkyl or aryl tellurolate anion occurs onto an activated alkyne with subsequent trapping of a vinyl anion with electrophiles (aldehydes and ketones) other than a proton. This process provides an efficient regio- and stereospecific route to tri- and tetrasubstituted alkenes. Methodologically significant examples of this chemistry were studied in which aryl and alkyl tellurolate anions were added to ω-keto alkynyl esters in a Michael reaction, and the incipient vinyl anions were trapped intramolecularly by the internal aldehydes. The reactive centers were tethered by different lengths of alkyl chains to form highly functionalized five-, six-, seven-, and eight-membered rings in modest to good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0110146