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Synfacts 2023; 19(01): 0061
DOI: 10.1055/s-0042-1753171
Metals in Synthesis

Intramolecular Nucleopalladation/Carbonylation of Alcohol-Tethered Alkenes

Authors

    Rezensent(en):

  • Mark Lautens

  • Jonathan Bajohr

Semmelhack MF, *, Bodurow C. Princeton University, USA
Intramolecular Alkoxypalladation/Carbonylation of Alkenes.

J. Am. Chem. Soc. 1984;
106: 1496-1498
DOI: 10.1021/ja00317a059
CrossrefSuche in Google Scholar
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Key words

palladium catalysis - carbonylation - nucleopalladation

Significance

Pyran and furan rings are frequently encountered in biologically relevant molecules. Variations of this reaction reported by Semmelhack and Bodurow in 1984 have been applied in numerous natural product total syntheses.


 

Comment

The authors demonstrated that alkene geometry and substitution patterns play a dominant role in the selectivity for the formation of five- or six-membered rings. Additionally, no 7-endo ­cyclizations were observed for suitable substrates.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
16. Dezember 2022

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