RT Journal Article
T1 Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters
A1 Arribas Domingo, Andrés
A1 Calvelo Souto, Martín
A1 Fernández Fernández, David
A1 Rodrigues, Catarina A. B.
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
K1 C-H activation
K1 Enantioselective
K1 Heterocycles
K1 Hydrocarbonation
K1 Iridium
AB We report a versatile, highly enantioselective intramolecular hydrocarbonation reaction that provides a direct access to heteropolycyclic systems bearing chiral quaternary carbon stereocenters. The method, which relies on an iridium(I)/bisphosphine chiral catalyst, is particularly efficient for the synthesis of five-, six- and seven-membered fused indole and pyrrole products, bearing one and two stereocenters, with enantiomeric excesses of up to >99 %. DFT computational studies allowed to obtain a detailed mechanistic profile and identify a cluster of weak non-covalent interactions as key factors to control the enantioselectivity
PB Wiley
SN 1433-7851
YR 2021
FD 2021
LK http://hdl.handle.net/10347/26623
UL http://hdl.handle.net/10347/26623
LA eng
NO Arribas, A., Calvelo, M., Fernández, D.F., Rodrigues, C.A.B., Mascareñas, J.L. and López, F. (2021), Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters. Angew. Chem. Int. Ed.. https://doi.org/10.1002/anie.202105776
NO This work received financial support from the Spanish MINECO (SAF2016-76689-R, PID2019-108624RB-I00, CTQ2017-84767-P, PID2020-118579GB-I00), the Xunta de Galicia (ED431C 2017/19, 2015-CP082, Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03, a predoctoral Fellowship to A. A. and M. C. and a postdoctoral Fellowship to D. F. F, ED481B-2019-005) and the ERDF, ERC (Adv. Grant No. 340055). The Orfeo-Cinqa network (CTQ2016-81797-REDC)
DS Minerva
RD 28 abr 2026