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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Veröffentlicht in:Journal of the American Chemical Society 2013-05, Vol.135 (18), p.6802-6805
Hauptverfasser: Spangler, Jillian E, Davies, Huw M. L
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja4025337