Atroposelective Haloamidation of Indoles with Amino Acid Derivatives and Hypohalides

An atroposelective coupling of indoles with chiral amino acid-based sulfonamides mediated by hypohalides is described. A series of 2-amido-3-haloindoles with a C–N chiral axis are delivered using this strategy. The C3 halogen atoms can facilitate further transformation. Various functionalities, such...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 21; pp. 8819 - 8823
Main Authors Li, Zhaojie, Tang, Menghan, Hu, Chenyang, Yu, Shouyun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYTIC ENANTIOSELECTIVE SYNTHESIS
LIGANDS
ASYMMETRIC ALLYLIC ALKYLATION
CONSTRUCTION
RESOLUTION
ARYLATION
N-ALLYLATION
STEREOSELECTIVE-SYNTHESIS
NON-BIARYL ATROPISOMERS
AXIALLY CHIRAL ANILIDES
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Summary:An atroposelective coupling of indoles with chiral amino acid-based sulfonamides mediated by hypohalides is described. A series of 2-amido-3-haloindoles with a C–N chiral axis are delivered using this strategy. The C3 halogen atoms can facilitate further transformation. Various functionalities, such as carbonyl, phosphine, aryl, and alkenyl groups, can be introduced into the C3 position of indoles. These structurally diverse and axially chiral indole derivatives can find further synthetic utilities. It can be exemplified with an axially chiral phosphine, which serves as a ligand in Pd-catalyzed cross couplings.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03456