Concepedia

Enantioselective Construction of Spiroindolenines by Ir-Catalyzed Allylic Alkylation Reactions

Qing‐Feng Wu, Hu He, Wenbo Liu, Shu‐Li You

Journal of the American Chemical Society · 2010 · 379 citations · 28 references

DOI

Concepts

Abstract

With 2-methyl-1,2,3,4-tetrahydroquinoline-derived phosphoramidite ligand (R,R(a))-L(6), Ir-catalyzed intramolecular C-3 allylic alkylation of indoles has been realized to afford highly enantioenriched spiroindolenine derivatives in 92-98% yields with up to >99/1 dr and 97% ee.

References

28

Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1<i>H</i>-Indoles Using Trialkylboranes

Barry M. Trost, Jean Quancard · Journal of the American Chemical Society · 2006 · 532 citations

, , +9

Iridium-catalysed asymmetricallylic substitutions

Günter Helmchen, Axel Dahnz, Pierre Dübon et al. · Chemical Communications · 2006 · 495 citations

, , +13

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Joel F. Austin, Sung-Gon Kim, Christopher J. Sinz et al. · Proceedings of the National Academy of Sciences · 2004 · 464 citations · Full text

, , +13

Pd-Catalyzed C3-Selective Allylation of Indoles with Allyl Alcohols Promoted by Triethylborane

Masanari Kimura, Makoto Futamata, Ryutaro Mukai et al. · Journal of the American Chemical Society · 2005 · 382 citations

, , +10

Regio- and Enantioselective Allylic Amination of Achiral Allylic Esters Catalyzed by an Iridium−Phosphoramidite Complex

Toshimichi Ohmura, John F. Hartwig · Journal of the American Chemical Society · 2002 · 371 citations

, , +13