Synthesis of α‐Quaternary β‐Lactams via Copper‐Catalyzed Enantioconvergent Radical C(sp3)−C(sp2) Cross‐Coupling with Organoboronate Esters

The copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the synthetically valuable α‐quaternary β‐lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters bet...

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Published inAngewandte Chemie International Edition Vol. 62; no. 2; pp. e202214709 - n/a
Main Authors Wang, Fu‐Li, Liu, Lin, Yang, Chang‐Jiang, Luan, Cheng, Yang, Jing, Chen, Ji‐Jun, Gu, Qiang‐Shuai, Li, Zhong‐Liang, Liu, Xin‐Yuan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 09.01.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Asymmetric Catalysis
beta-Lactams
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Construction
Copper
Copper - chemistry
Cross coupling
Electrons
Esters
Physical Sciences
Radical Chemistry
Science & Technology
β-Lactam
TRANSITION-METAL CATALYSIS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
beta-Lactam
Radical Chemistry
SUBSTITUTION-REACTIONS
ARYLBORONIC ACIDS
ALKYL-HALIDES
Asymmetric Catalysis
TRANSMETALATION
Cross-Coupling
Copper
DERIVATIVES
ACCESS
CYCLIZATION
β-Lactam
Online AccessGet full text

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Abstract The copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the synthetically valuable α‐quaternary β‐lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N‐ligand catalyst to forge the sterically congested chiral C(sp3)−C(sp2) bond via a single‐electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross‐coupling reactions. Copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary alkyl bromides with organoboronate esters is developed to access synthetically valuable α‐quaternary chiral β‐lactams. The success of this work relies on the utilization of chiral N,N,N‐ligands to forge the sterically congested C(sp3)−C(sp2) bonds.
AbstractList The copper-catalyzed enantioconvergent radical C(sp3 )-C(sp2 ) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the synthetically valuable α-quaternary β-lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N-ligand catalyst to forge the sterically congested chiral C(sp3 )-C(sp2 ) bond via a single-electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross-coupling reactions.The copper-catalyzed enantioconvergent radical C(sp3 )-C(sp2 ) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the synthetically valuable α-quaternary β-lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N-ligand catalyst to forge the sterically congested chiral C(sp3 )-C(sp2 ) bond via a single-electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross-coupling reactions.
The copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the synthetically valuable α‐quaternary β‐lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N‐ligand catalyst to forge the sterically congested chiral C(sp3)−C(sp2) bond via a single‐electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross‐coupling reactions.Dedicated to Professor Keiji Maruoka on the occasion of his 70th birthday
The copper-catalyzed enantioconvergent radical C(sp(3))-C(sp(2)) cross-coupling of tertiary alpha-bromo-beta-lactams with organoboronate esters could provide the synthetically valuable alpha-quaternary beta-lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N-ligand catalyst to forge the sterically congested chiral C(sp(3))-C(sp(2)) bond via a single-electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross-coupling reactions.
The copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the synthetically valuable α‐quaternary β‐lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N‐ligand catalyst to forge the sterically congested chiral C(sp3)−C(sp2) bond via a single‐electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross‐coupling reactions. Copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary alkyl bromides with organoboronate esters is developed to access synthetically valuable α‐quaternary chiral β‐lactams. The success of this work relies on the utilization of chiral N,N,N‐ligands to forge the sterically congested C(sp3)−C(sp2) bonds.
The copper‐catalyzed enantioconvergent radical C(sp 3 )−C(sp 2 ) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the synthetically valuable α‐quaternary β‐lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N‐ligand catalyst to forge the sterically congested chiral C(sp 3 )−C(sp 2 ) bond via a single‐electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross‐coupling reactions.
The copper-catalyzed enantioconvergent radical C(sp )-C(sp ) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the synthetically valuable α-quaternary β-lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N-ligand catalyst to forge the sterically congested chiral C(sp )-C(sp ) bond via a single-electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross-coupling reactions.
Author Chen, Ji‐Jun
Yang, Chang‐Jiang
Li, Zhong‐Liang
Liu, Xin‐Yuan
Wang, Fu‐Li
Yang, Jing
Gu, Qiang‐Shuai
Luan, Cheng
Liu, Lin
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  organization: Southern University of Science and Technology
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Issue 2
Keywords TRANSITION-METAL CATALYSIS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
beta-Lactam
Radical Chemistry
SUBSTITUTION-REACTIONS
ARYLBORONIC ACIDS
ALKYL-HALIDES
Asymmetric Catalysis
TRANSMETALATION
Cross-Coupling
Copper
DERIVATIVES
ACCESS
CYCLIZATION
β-Lactam
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Notes These authors contributed equally to this work.
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PublicationCentury 2000
PublicationDate January 9, 2023
PublicationDateYYYYMMDD 2023-01-09
PublicationDate_xml – month: 01
  year: 2023
  text: January 9, 2023
  day: 09
PublicationDecade 2020
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
– name: Germany
– name: Weinheim
PublicationTitle Angewandte Chemie International Edition
PublicationTitleAbbrev ANGEW CHEM INT EDIT
PublicationTitleAlternate Angew Chem Int Ed Engl
PublicationYear 2023
Publisher Wiley
Wiley Subscription Services, Inc
Publisher_xml – name: Wiley
– name: Wiley Subscription Services, Inc
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Snippet The copper‐catalyzed enantioconvergent radical C(sp3)−C(sp2) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the...
The copper‐catalyzed enantioconvergent radical C(sp 3 )−C(sp 2 ) cross‐coupling of tertiary α‐bromo‐β‐lactams with organoboronate esters could provide the...
The copper-catalyzed enantioconvergent radical C(sp(3))-C(sp(2)) cross-coupling of tertiary alpha-bromo-beta-lactams with organoboronate esters could provide...
The copper-catalyzed enantioconvergent radical C(sp )-C(sp ) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the...
The copper-catalyzed enantioconvergent radical C(sp3 )-C(sp2 ) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the...
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StartPage e202214709
SubjectTerms Asymmetric Catalysis
beta-Lactams
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Construction
Copper
Copper - chemistry
Cross coupling
Electrons
Esters
Physical Sciences
Radical Chemistry
Science & Technology
β-Lactam
Title Synthesis of α‐Quaternary β‐Lactams via Copper‐Catalyzed Enantioconvergent Radical C(sp3)−C(sp2) Cross‐Coupling with Organoboronate Esters
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202214709
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https://www.ncbi.nlm.nih.gov/pubmed/36357331
https://www.proquest.com/docview/2759968461
https://www.proquest.com/docview/2735870687
Volume 62
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