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University of Groningen Catalytic asymmetric carbon-carbon bond forming methodologies for synthesis of chiral N- containing heterocycles and chiral carboxamides Guo, Yafei

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University of Groningen

Catalytic asymmetric carbon-carbon bond forming methodologies for synthesis of chiral N-containing heterocycles and chiral carboxamides

Guo, Yafei

DOI:

10.33612/diss.147535855

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date: 2020

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Guo, Y. (2020). Catalytic asymmetric carbon-carbon bond forming methodologies for synthesis of chiral N-containing heterocycles and chiral carboxamides. University of Groningen.

https://doi.org/10.33612/diss.147535855

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List of abbreviations

ACA: asymmetric conjugate addition AAA: Asymmetric allylic alkylation CA: conjugate addition

calcd.: calculated DCM: dichloromethane

DMF: N,N-dimethylformamide

ee: enantiomeric excess

ESI: electrospray ionization

HMBC: heteronuclear multiple bond correlation spectroscopy HOESY: heteronuclear overhauser effect spectroscopy

HPLC: high performance liquid chromatography HRMS: high-resolution mass spectrometry LA: Lewis acid

m-CPBA: 3-chloroperbenzoic acid

MTBE: methyl-tert-butylether NMR: nuclear magnetic resonance NOE: nuclear overhauser effect ppm: parts per million

Rac: racemic

ROESY: rotating frame overhause effect spectroscopy RT: room temperature

THF: tetrahydrofuran

TLC: thin layer chromatography TMS: trimethylsilyl

TMSBr: trimethylsilyl bromide TMSCl: trimethylsilyl chloride

TMSOTf: trimethylsilyl trifluorosulfonate

Tol-Binap: 2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl UV: ultraviolet

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