Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8439-8444Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03164
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Funding
- Saarland University
- DFG [Ka 880/13-1, 500-447298507]
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Allylzinc reagents are versatile nucleophiles that exhibit excellent E selectivities in Matteson homologations. The resulting allylated boronic esters can be further converted into trifluoroborates or subjected to additional homologations, providing a useful tool for organic synthesis.
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.
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