RT Journal Article
T1 Stereoselective Synthesis of Highly Substituted 1,3-Dienes via “à la carte” Multifunctionalization of Borylated Dendralenes
A1 Rivera Chao, Eva
A1 Fañanás-Mastral, Martín
K1 1,3-dienes
K1 Boron
K1 Carbolithiation
K1 Dendralenes
K1 Multicomponent reactions
AB 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.
PB Wiley
SN 1433-7851
YR 2021
FD 2021
LK http://hdl.handle.net/10347/26627
UL http://hdl.handle.net/10347/26627
LA eng
NO E. Rivera-Chao, M. Fañanás-Mastral, Angew. Chem. Int. Ed. 2021, 60, 16922.
NO Financial support from the AEI (CTQ2017-88451-R), Xunta de Galicia (ED431C 2018/04; Centro singular de investigación de Galicia accreditation 2019–2022, ED431G 2019/03) and the European Union (European Regional Development Fund—ERDF) is gratefully acknowledged. E. R.-C. thanks Xunta de Galicia for a predoctoral fellowship
DS Minerva
RD 27 abr 2026