Scalable Synthesis of β-Lactamase Inhibitor QPX7728 by Sequential Nickel-Catalyzed Boron Insertion into a Benzofuran Substrate and Enantioselective Cyclopropanation of the Resulting Vinylboronate
We report the scalable, high-yielding, and highly selective synthesis of the β-lactamase inhibitor QPX7728 featuring two key synthetic steps: nickel-catalyzed boron insertion of benzofuran 1 followed by enantioselective cyclopropanation of the resulting cyclic vinylboronate 2. The identification of the key reagents (catalyst and chiral auxiliary) for both steps relied on the use of high-throughput experimentation. Further optimization allowed for the cost-effective and scalable production of QPX7728.
Boyer, Serge H.,De Vries, André H. M.,Dielemans, J. A. Hubertus,Gnahn, Matthias,Gonzalez-De-Castro, Angela,Hecker, Scott J.,Lefort, Laurent,Sch?rghuber, Julia,Steinhofer, Stefan,Zhu, Zuolin
supporting information
(2021/10/01)
NICKEL PRE-CATALYSTS AND RELATED COMPOSITIONS AND METHODS
Described herein are nickel pre-catalysts and related compositions and methods. The nickel pre-catalysts may be activated to form catalysts which may be utilized in organic reactions.
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Page/Page column 40
(2015/05/26)
Synthesis and fluxional behavior of [bis(trialkylphosphine)nickelio]anthracene (alkyl = Et, Bu)
The title compounds were prepared from the respective (R3P)2NiCl2 complexes and magnesium-anthracene-(THF)3 (or anthracene in the presence of Mg or C8K). The assignment of the anthracene proton NMR si
Stanger, Amnon,Vollhardt, K. Peter C.
p. 317 - 320
(2008/10/08)
Reaction of P-Halogeno-phospha-alkenes with Alkene Complexes of Nickel and Platinum: η2-Co-ordination and Unusual Oxidative Addition Behaviour
Phospha-alkenes X-P=CTMS2 (X = F, Cl, I; TMS = SiMe3) display different reaction behaviour towards metal complexes (Bu3P)2Ni(cod) (cod = cyclo-octa-1,5-diene) or (PH3P)2Pt(C2H4), respectively, undergoing either co-ordination to give η2-phospha-
Gudat, D.,Meidine, M. F.,Nixon, J. F.,Niecke, E.
p. 1206 - 1207
(2007/10/02)
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