RT Journal Article
T1 Copper-Catalyzed Enantioselective Borylative Allyl–Allyl Coupling of Allenes and Allylic gem-Dichlorides
A1 Piñeiro-Suárez, Martín
A1 Álvarez-Constantino, Andrés M.
A1 Fañanás-Mastral, Martín
K1 Copper
K1 Allylboration
K1 Asymmetric catalysis
K1 Allenes
K1 Multifunctional compounds
K1 Noncovalent interactions
AB A catalytic asymmetric reaction between allenes, bis(pinacolato)diboron, and allylic gem-dichlorides is reported. The method involves the coupling of a catalytically generated allyl copper species with the allylic gem-dichloride and provides chiral internal 1,5-dienes featuring (Z)-configured alkenyl boronate and alkenyl chloride units with high levels of chemo-, regio-, enantio-, and diastereoselectivity. The synthetic utility of the products is demonstrated with the synthesis of a range of optically active compounds. DFT calculations reveal key noncovalent substrate–ligand interactions that account for the enantioselectivity outcome and the diastereoselective formation of the (Z)-alkenyl chloride
PB ACS
SN 2155-5435
YR 2023
FD 2023-04-10
LK http://hdl.handle.net/10347/31152
UL http://hdl.handle.net/10347/31152
LA eng
NO ACS Catalysis 2023 13 (8), 5578-5583
NO Financial support from the AEI (PID2020-118237RB-I00), European Research Council (863914), Xunta de Galicia (ED431C 2022/27; Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03), and the European Regional Development Fund (ERDF) is gratefully acknowledged. M.P.-S. and A.M.A.-C. thank AEI and Xunta de Galicia, respectively, for predoctoral fellowships. We also thank the use of RIAIDT-USC analytical facilities and CESGA (Xunta de Galicia) for computational time
DS Minerva
RD 24 abr 2026