Titanocene‐Catalyzed Radical Opening of N‐Acylated Aziridines

Aziridines activated by N‐acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carb...

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Published inAngewandte Chemie International Edition Vol. 56; no. 41; pp. 12654 - 12657
Main Authors Zhang, Yong‐Qiang, Vogelsang, Elisabeth, Qu, Zheng‐Wang, Grimme, Stefan, Gansäuer, Andreas
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 02.10.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Acylation
aziridines
Catalysis
Chemistry
Chemistry, Multidisciplinary
conjugate addition
Electron transfer
Physical Sciences
radical ring opening
reduction
Ring opening
Science & Technology
titanocenes
aziridines
AUXILIARY BASIS-SETS
EPOXIDE
conjugate addition
radical ring opening
ELECTRON-TRANSFER
ZETA VALENCE QUALITY
titanocenes
ATOMS
AMINOKETYL RADICALS
reduction
AMIDE BOND
UMPOLUNG
CYCLIZATION
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Abstract Aziridines activated by N‐acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations. Useful intermediates for intermolecular additions, reductions, and cyclizations are obtained with excellent regioselectivity via β‐amido‐substituted radicals catalytically generated from N‐acyl aziridines. DFT calculations indicate that the ring opening is concerted rather than stepwise as previously postulated.
AbstractList Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations.
Aziridines activated by N‐acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations. Useful intermediates for intermolecular additions, reductions, and cyclizations are obtained with excellent regioselectivity via β‐amido‐substituted radicals catalytically generated from N‐acyl aziridines. DFT calculations indicate that the ring opening is concerted rather than stepwise as previously postulated.
Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations.Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations.
Author Zhang, Yong‐Qiang
Vogelsang, Elisabeth
Qu, Zheng‐Wang
Gansäuer, Andreas
Grimme, Stefan
Author_xml – sequence: 1
  givenname: Yong‐Qiang
  surname: Zhang
  fullname: Zhang, Yong‐Qiang
  organization: Universität Bonn
– sequence: 2
  givenname: Elisabeth
  surname: Vogelsang
  fullname: Vogelsang, Elisabeth
  organization: Universität Bonn
– sequence: 3
  givenname: Zheng‐Wang
  surname: Qu
  fullname: Qu, Zheng‐Wang
  organization: Universität Bonn
– sequence: 4
  givenname: Stefan
  surname: Grimme
  fullname: Grimme, Stefan
  organization: Universität Bonn
– sequence: 5
  givenname: Andreas
  surname: Gansäuer
  fullname: Gansäuer, Andreas
  email: andreas.gansaeuer@uni-bonn.de
  organization: Universität Bonn
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Issue 41
Keywords aziridines
AUXILIARY BASIS-SETS
EPOXIDE
conjugate addition
radical ring opening
ELECTRON-TRANSFER
ZETA VALENCE QUALITY
titanocenes
ATOMS
AMINOKETYL RADICALS
reduction
AMIDE BOND
UMPOLUNG
CYCLIZATION
Language English
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2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Snippet Aziridines activated by N‐acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic...
Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic...
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SubjectTerms Acylation
aziridines
Catalysis
Chemistry
Chemistry, Multidisciplinary
conjugate addition
Electron transfer
Physical Sciences
radical ring opening
reduction
Ring opening
Science & Technology
titanocenes
Title Titanocene‐Catalyzed Radical Opening of N‐Acylated Aziridines
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201707673
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https://www.ncbi.nlm.nih.gov/pubmed/28833905
https://www.proquest.com/docview/1943038189
https://www.proquest.com/docview/1932169365
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