Asymmetric Synthesis of Axially Chiral Anilides via Organocatalytic Atroposelective N‑Acylation

A highly atroposelective N-acylation reaction of aniline-derived sulfonamides has been developed with chiral isothiourea as the catalyst. This approach provides a facile and efficient route to an array of atropoisomeric sulfonyl substituted anilide products in good yields with high to excellent enan...

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Published inOrganic letters Vol. 22; no. 14; pp. 5331 - 5336
Main Authors Li, Dawei, Wang, Sijing, Ge, Shulin, Dong, Shunxi, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYTIC ENANTIOSELECTIVE SYNTHESIS
ACTIVE ATROPISOMERIC ANILIDES
HOMOBENZOTETRAMISOLE
CONSTRUCTION
(S)-METOLACHLOR
EFFICIENT SYNTHESIS
PIVALIC ANHYDRIDE
SWITCH
ARYL
DYNAMIC KINETIC RESOLUTION
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Summary:A highly atroposelective N-acylation reaction of aniline-derived sulfonamides has been developed with chiral isothiourea as the catalyst. This approach provides a facile and efficient route to an array of atropoisomeric sulfonyl substituted anilide products in good yields with high to excellent enantioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01581