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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Summary: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.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02935