Highly Chemo‐ and Stereoselective Catalyst‐Controlled Allylic C−H Insertion and Cyclopropanation Using Donor/Donor Carbenes

The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles wi...

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Published inAngewandte Chemie International Edition Vol. 57; no. 38; pp. 12405 - 12409
Main Authors Zhu, Dong, Chen, Lianfen, Zhang, He, Ma, Zhiqiang, Jiang, Huanfeng, Zhu, Shifa
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.09.2018
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
asymmetric catalysis
Carbenes
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
cyclopropanation
Cyclopropane
heterocycles
Insertion
Physical Sciences
Rhodium compounds
ruthenium
Science & Technology
Stereoselectivity
ALPHA-DIAZOCARBONYL COMPOUNDS
ORGANIC-SYNTHESIS
PROPARGYLIC ESTERS
ASYMMETRIC-SYNTHESIS
carbenes
DIAZO-COMPOUNDS
asymmetric catalysis
NONDIAZO APPROACH
ruthenium
CHIRAL DIRHODIUM(II) CATALYSTS
cyclopropanation
heterocycles
METAL CARBENE
MIGRATORY INSERTION
ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION
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Abstract The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane‐fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee. Rh versus Ru: The highly chemo‐, enantio‐ and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes is reported. The RuII/Pybox complex selectively catalyzes the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles. Chiral dirhodium(II) tetracarboxylates, however, selectively catalyzed the intramolecular cyclopropanation.
AbstractList The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane‐fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee. Rh versus Ru: The highly chemo‐, enantio‐ and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes is reported. The RuII/Pybox complex selectively catalyzes the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles. Chiral dirhodium(II) tetracarboxylates, however, selectively catalyzed the intramolecular cyclopropanation.
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII /Pybox complex selectively catalyzed the intramolecular allylic C-H insertion, providing vinyl-substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane-fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee.The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII /Pybox complex selectively catalyzed the intramolecular allylic C-H insertion, providing vinyl-substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane-fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee.
The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane‐fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee.
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are reported. The Ru /Pybox complex selectively catalyzed the intramolecular allylic C-H insertion, providing vinyl-substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane-fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee.
The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are reported. The Ru II /Pybox complex selectively catalyzed the intramolecular allylic C−H insertion, providing vinyl‐substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99 % ee . Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane‐fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97 % ee .
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are reported. The Ru-II/Pybox complex selectively catalyzed the intramolecular allylic C-H insertion, providing vinyl-substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99% ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane-fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97% ee.
Author Jiang, Huanfeng
Ma, Zhiqiang
Chen, Lianfen
Zhu, Dong
Zhu, Shifa
Zhang, He
Author_xml – sequence: 1
  givenname: Dong
  surname: Zhu
  fullname: Zhu, Dong
  organization: South China University of Technology
– sequence: 2
  givenname: Lianfen
  surname: Chen
  fullname: Chen, Lianfen
  organization: South China University of Technology
– sequence: 3
  givenname: He
  surname: Zhang
  fullname: Zhang, He
  organization: South China University of Technology
– sequence: 4
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  surname: Ma
  fullname: Ma, Zhiqiang
  organization: South China University of Technology
– sequence: 5
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  fullname: Jiang, Huanfeng
  organization: South China University of Technology
– sequence: 6
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  orcidid: 0000-0001-5172-7152
  surname: Zhu
  fullname: Zhu, Shifa
  email: zhusf@scut.edu.cn
  organization: South China University of Technology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30059187$$D View this record in MEDLINE/PubMed
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IsPeerReviewed true
IsScholarly true
Issue 38
Keywords ALPHA-DIAZOCARBONYL COMPOUNDS
ORGANIC-SYNTHESIS
PROPARGYLIC ESTERS
ASYMMETRIC-SYNTHESIS
carbenes
DIAZO-COMPOUNDS
asymmetric catalysis
NONDIAZO APPROACH
ruthenium
CHIRAL DIRHODIUM(II) CATALYSTS
cyclopropanation
heterocycles
METAL CARBENE
MIGRATORY INSERTION
ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION
Language English
License 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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ObjectType-Feature-2
content type line 14
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PublicationTitle Angewandte Chemie International Edition
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Snippet The highly chemo‐, enantio‐, and diastereoselective catalyst‐controlled intramolecular allylic C−H insertion and cyclopropanation of donor/donor carbenes are...
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are...
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SubjectTerms asymmetric catalysis
Carbenes
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
cyclopropanation
Cyclopropane
heterocycles
Insertion
Physical Sciences
Rhodium compounds
ruthenium
Science & Technology
Stereoselectivity
Title Highly Chemo‐ and Stereoselective Catalyst‐Controlled Allylic C−H Insertion and Cyclopropanation Using Donor/Donor Carbenes
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https://www.ncbi.nlm.nih.gov/pubmed/30059187
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Volume 57
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