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Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides

Author:
Iwamoto, Takahiro, Okuzono, Chiemi, Adak, Laksmikanta, Jin, Masayoshi, Nakamura, Masaharu
Source:
Chemical communications 2019 v.55 no.8 pp. 1128-1131
ISSN:
1364-548X
Subject:
Suzuki reaction, acids, enantioselectivity, ferrous chloride, ligands, lithium, nonsteroidal anti-inflammatory agents, optical isomerism, organobromine compounds
Abstract:
The first iron-catalysed enantioselective Suzuki–Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl₂ and (R,R)-QuinoxP*, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP* is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.
Agid:
6269289