Asymmetric Friedel-Crafts Addition of Indoles to N-Sulfonyl Aldimines

Y.-X. Jia; J.-H. Xie; H.-F. Duan; L.-X. Wang; Q.-L. Zhou

doi:10.1055/s-2006-934470

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synfacts 2006(6): 0576-0576
DOI: 10.1055/s-2006-934470

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Asymmetric Friedel-Crafts Addition of Indoles to N-Sulfonyl Aldimines

Contributor(s): Mark Lautens, Frédéric Ménard
Y.-X. Jia, J.-H. Xie, H.-F. Duan, L.-X. Wang, Q.-L. Zhou*
Nankai UniVersity, P. R. of China

Weitere Informationen

Publikationsverlauf

Publikationsdatum:
19. Mai 2006 (online)

Lizenzen und Reprints

Significance

This Cu(II)-catalyzed addition of unprotected indoles to N-sulfonyl aldimines provides a simple approach to optically active 3-indolylmethanamine derivatives. This reaction showed remarkable selectivity for the position 3 of the indole. Noteworthy is the reactivity of even sterically demanding substrates (Ar = 2,6-Cl₂C₆H₃: 47%). This reaction is favored for electron-poor aromatic aldimines (EWG = 94%, EDG = 47%).