RT Journal Article
T1 Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes
A1 Verdugo Leal, Felipe Ignacio
A1 Villarino Palmaz, Lara
A1 Durán, Juan
A1 Gulías Costa, Moisés
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
K1 Alkylidenecyclopropane
K1 Asymmetric
K1 Cycloaddition
K1 Enantioselective
K1 Palladium
K1 Phosphoramidite
AB We report a highly enantioselective [3C + 2C] intramolecular cycloaddition of alkylidenecyclopropanes (ACPs) and alkenes. The best results are obtained by using sterically demanding chiral phosphoramidite ligands derived from Vapol. Moreover, we also show that related, but less bulky, phosphoramidites can also lead to very effective [4C + 3C] cycloadditions when dienes, instead of alkenes, are used as reacting partners. The reactions provide a practical, simple, and selective access to optically active, synthetically appealing 5,5- and 5,7-bicyclic systems
PB American Chemical Society
SN 2155-5435
YR 2018
FD 2018-06-04
LK http://hdl.handle.net/10347/17410
UL http://hdl.handle.net/10347/17410
LA eng
NO Verdugo, F., Villarino, L., Durán, J., Gulías, M., Mascareñas, J., & López, F. (2018). Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 8(7), 6100-6105. doi: 10.1021/acscatal.8b01296
NO NOTICE: This is the peer reviewed version of the following article: Felipe Verdugo, Lara Villarino, Juan Durán, Moisés Gulías, José L. Mascareñas and Fernando López (2018), Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intra-molecular Cycloadditions of Alkylidenecyclopropanes. ACS Catalysis, 2018, 8, 6100–6105 [DOI: 10.1021/acscatal.8b01296]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
NO This work received financial support from the spanish MINECO grants (Nos. SAF2016-76689-R, CTQ2016-77047-P, CTQ2017-84767-P, FPU to L.V. and J.D.), Xunta de Galicia (Nos. ED431C 2017/19, 2015-CP082, and Centro Singular de Investigación de Galicia accreditation 2016-2019 ED431G/09), the ERDF and ERC (Adv. Grant No. 340055). The Orfeo-Cinqa network CTQ2016-81797-REDC, CONICYT-Becas Chile (Ph.D. grant to F.V.) and Sarah Walker (preliminary work) are also acknowledged
DS Minerva
RD 22 abr 2026