Catalytic Asymmetric Synthesis of Pyrroloindolines via a Rhodium(II)-Catalyzed Annulation of Indoles

Herein we report the synthesis of pyrrolo­indolines via a catalytic enantio­selective formal [3+2] cycloaddition of C(3)-substituted indoles. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbenoid precursors and the rhodium(II)-tetracarboxylate catalyst Rh2(S-PTAD)4. A variety of a...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 18; pp. 6802 - 6805
Main Authors Spangler, Jillian E, Davies, Huw M. L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.05.2013
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Pyrroles - chemical synthesis
Pyrroles - chemistry
Rhodium - chemistry
Science & Technology
Stereoisomerism
AZAVINYL CARBENES
TRYPTOPHAN
ENANTIOSELECTIVE SYNTHESIS
HETEROCYCLES
CONCISE TOTAL-SYNTHESIS
CONSTRUCTION
CYCLOPROPANATION
ARYL PYRROLOINDOLINES
RHODIUM CARBENOIDS
ALKALOIDS
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Summary:Herein we report the synthesis of pyrrolo­indolines via a catalytic enantio­selective formal [3+2] cycloaddition of C(3)-substituted indoles. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbenoid precursors and the rhodium(II)-tetracarboxylate catalyst Rh2(S-PTAD)4. A variety of aryl-substituted pyrrolo­indolines were prepared in good yields and with high levels of enantio­induction.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja4025337