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Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations.

Andler, Oliver
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Kazmaier, Uli
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2021-10-11
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Abstract
Allylzinc reagents are versatile nucleophiles that can be used in Matteson homologations. The linear substitution products are formed almost exclusively, and excellent E selectivities are observed in reactions of reagents with sterically demanding or aryl substituents on the double bond. The allylated boronic esters obtained can be converted into trifluoroborates or subjected to further homologations. Ozonolysis of the double bond provides aldehydes or ketones, and therefore, allylzinc reagents are useful acetaldehyde or ketone enolate equivalents.
Citation
Org Lett. 2021 Nov 5;23(21):8439-8444. doi: 10.1021/acs.orglett.1c03164. Epub 2021 Oct 11.
Affiliation
HIPS, Helmholtz-Institut für Pharmazeutische Forschung Saarland, Universitätscampus E8.1 66123 Saarbrücken, Germany.
Publisher
ACS
Journal
Organic letters
URI
http://hdl.handle.net/10033/623103
DOI
10.1021/acs.orglett.1c03164
PubMed ID
34633200
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Article
Language
en
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1523-7052
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Attribution 4.0 International
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