Entry to Chiral 1,1,2,3-Tetrasubstituted Arylcyclopropanes by Pd(II)-Catalyzed Arylation via Directing Group-Mediated C(sp3)‑H Activation

Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd­(II)-catalyzed arylation via directing group-mediated C­(sp3)-H activation. The key aspect for the effective arylation was control of the substrate con...

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Published inJournal of organic chemistry Vol. 82; no. 5; pp. 2535 - 2544
Main Authors Hoshiya, Naoyuki, Kondo, Moemi, Fukuda, Hayato, Arisawa, Mitsuhiro, Uenishi, Jun’ichi, Shuto, Satoshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.03.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEREOSELECTIVE CYCLOPROPANATION
CONFORMATIONAL RESTRICTION
POTENT
CARBON
PRIVILEGED STRUCTURES
ALKYLATION
RING
PALLADIUM-CATALYZED ARYLATION
AUXILIARY
C-H BONDS
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Abstract Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd­(II)-catalyzed arylation via directing group-mediated C­(sp3)-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
AbstractList Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd(II)-catalyzed arylation via directing group-mediated C(sp3)-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd(II)-catalyzed arylation via directing group-mediated C(sp )-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd­(II)-catalyzed arylation via directing group-mediated C­(sp3)-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd(ll)-catalyzed arylation via directing group -mediated C(sp(3))-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
Author Arisawa, Mitsuhiro
Kondo, Moemi
Shuto, Satoshi
Fukuda, Hayato
Hoshiya, Naoyuki
Uenishi, Jun’ichi
AuthorAffiliation Hokkaido University
Department of Pharmaceutical Chemistry
Faculty of Pharmaceutical Sciences
Osaka University
Graduate School of Pharmaceutical Sciences
Center for Research and Education on Drug Discovery
Kyoto Pharmaceutical University
AuthorAffiliation_xml – name: Department of Pharmaceutical Chemistry
– name: Osaka University
– name: Graduate School of Pharmaceutical Sciences
– name: Hokkaido University
– name: Kyoto Pharmaceutical University
– name: Faculty of Pharmaceutical Sciences
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  surname: Shuto
  fullname: Shuto, Satoshi
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  organization: Hokkaido University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28120614$$D View this record in MEDLINE/PubMed
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Issue 5
Keywords STEREOSELECTIVE CYCLOPROPANATION
CONFORMATIONAL RESTRICTION
POTENT
CARBON
PRIVILEGED STRUCTURES
ALKYLATION
RING
PALLADIUM-CATALYZED ARYLATION
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Snippet Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using...
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SubjectTerms Chemistry
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Physical Sciences
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Title Entry to Chiral 1,1,2,3-Tetrasubstituted Arylcyclopropanes by Pd(II)-Catalyzed Arylation via Directing Group-Mediated C(sp3)‑H Activation
URI http://dx.doi.org/10.1021/acs.joc.6b02935
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https://www.ncbi.nlm.nih.gov/pubmed/28120614
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Volume 82
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