Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis

The bis(trifluoromethane)sulfonimide (Tf2NH) catalyzed intramolecular hydroamidation of terminal alkynes is reported. The combination of Et3SiH and Tf2NH provides cis-1,3-disubstituted isoindolines and sultams in high yield (up to 98%) and high diastereoselectivity (up to 99:1 d.r.).

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 54; no. 80; pp. 11292 - 11295
Main Authors Tao, Ye, Gilbertson, Scott R.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.10.2018
Royal Society of Chemistry
Subjects
Alkynes
Catalysis
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoselectivity
Trifluoromethane
BRONSTED ACID
CHIRAL HOMOPROPARGYL SULFONAMIDES
ENANTIOSELECTIVE SYNTHESIS
NITROGEN-HETEROCYCLES
A-C
HYDROAMINATION
ALKYNES
EFFICIENT
CYCLIZATION
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Summary:The bis(trifluoromethane)sulfonimide (Tf2NH) catalyzed intramolecular hydroamidation of terminal alkynes is reported. The combination of Et3SiH and Tf2NH provides cis-1,3-disubstituted isoindolines and sultams in high yield (up to 98%) and high diastereoselectivity (up to 99:1 d.r.).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc04946g