Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 31, Pages 16922-16927Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202104741
Keywords
1,3-dienes; boron; carbolithiation; dendralenes; multicomponent reactions
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Funding
- AEI [CTQ2017-88451-R]
- Xunta de Galicia [ED431C 2018/04]
- Centro singular de investigacion de Galicia accreditation [ED431G 2019/03]
- European Union (European Regional Development Fund-ERDF)
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An efficient and modular approach has been developed for the synthesis of multifunctional tetrasubstituted 1,3-dienes with high levels of regio- and stereoselectivity. This method is based on a tetracomponent reaction involving a borylated dendralene, an organolithium reagent, and two different electrophiles. Mechanistic studies have revealed the pathway of this transformation.
Despite the high relevance of 1,3-dienes, stereoselective methods to access tetrasubstituted conjugated dienes are still scarce. We here report an efficient and modular approach that provides access to multifunctional tetrasubstituted 1,3-dienes with excellent levels of regio- and stereoselectivity. This methodology is based on a tetracomponent reaction between a borylated dendralene, an organolithium reagent and two different electrophiles. Mechanistic studies reveal that this transformation proceeds through a regio- and stereoselective carbolithiation/electrophilic trapping of an in situ formed dendralenic boron-ate complex, followed by a stereoretentive halodeborylation. The ease in which complex structural dienes can be accessed and their synthetic versatility highlight the importance and utility of this method.
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