Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation

A two-step conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides is described. In this procedure, arenes are converted to aryl boronic esters by iridium-catalyzed borylation, and the aryl boronic esters are converted to enantioenriched amines by subsequent rhodium-cata...

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Bibliographic Details
Published inTetrahedron Vol. 64; no. 29; pp. 6824 - 6830
Main Authors Boebel, Timothy A., Hartwig, John F.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.07.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IRIDIUM-CATALYZED BORYLATION
ASYMMETRIC-SYNTHESIS
ARYLBORONIC ESTERS
IMINES
COUPLING REACTION
ALPHA-AMINO-ACIDS
N-TERT-BUTANESULFINYL
ORGANOLITHIUM REAGENTS
ROOM-TEMPERATURE REACTIONS
C-H BONDS
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Summary:A two-step conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides is described. In this procedure, arenes are converted to aryl boronic esters by iridium-catalyzed borylation, and the aryl boronic esters are converted to enantioenriched amines by subsequent rhodium-catalyzed addition to chiral tert-butanesulfinimes. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.04.060