RT Journal Article
T1 Enantioselective Synthesis of α-Chiral Bicyclo[1.1.1]pentanes via Multicomponent Asymmetric Allylic Alkylation
A1 Barbeira-Arán, Sergio
A1 Sánchez-Sordo, Irene
A1 Fañanás-Mastral, Martín
A1 Barbeira Arán, Sergio
A1 Sánchez Sordo, Irene
A1 Fañanás-Mastral, Martín
K1 Alkyls
K1 Catalysts
K1 Phosphates
K1 Reagents
K1 Stereoselectivity
AB Bicyclo[1.1.1]pentanes (BCPs) have emerged as important structural motifs in drug design. However, asymmetric transformations that provide chiral BCPs bearing an adjacent stereocenter are still scarce. Here, we report a catalytic methodology for the enantioselective synthesis of α-chiral 1,3-difunctionalized BCPs from a three-component coupling of [1.1.1]propellane, a Grignard reagent, and an allylic phosphate. The reaction proceeds via the addition of the Grignard reagent to [1.1.1]propellane followed by an asymmetric N-heterocyclic carbene (NHC)-catalyzed allylic substitution of the resulting BCP–Grignard, providing a broad range of α-chiral BCPs with excellent levels of regioselectivity and enantioselectivity
PB ACS
SN 1523-7060
YR 2024
FD 2024-04-30
LK http://hdl.handle.net/10347/34985
UL http://hdl.handle.net/10347/34985
LA eng
NO Org. Lett. 2024, 26, 18, 3784–3789
NO Financial support from the Agencia Estatal de Investigación(AEI, PID2020-118237RB-I00), the European Research Council (863914), the Xunta de Galicia (ED431C 2022/27;Centro Singular de Investigación de Galicia Accreditation 2019−2022, ED431G 2019/03), and the European RegionalDevelopment Fund (ERDF) is gratefully acknowledged
DS Minerva
RD 27 abr 2026