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Synfacts 2023; 19(01): 0061
DOI: 10.1055/s-0042-1753171
DOI: 10.1055/s-0042-1753171
Metals in Synthesis
Intramolecular Nucleopalladation/Carbonylation of Alcohol-Tethered Alkenes
Semmelhack MF,
*,
Bodurow C.
Princeton University, USA
Intramolecular Alkoxypalladation/Carbonylation of Alkenes.
J. Am. Chem. Soc. 1984;
106: 1496-1498
DOI: 10.1021/ja00317a059.
Intramolecular Alkoxypalladation/Carbonylation of Alkenes.
J. Am. Chem. Soc. 1984;
106: 1496-1498
DOI: 10.1021/ja00317a059.
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.
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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.
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Publication History
Article published online:
16 December 2022
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