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. 2012 Nov 26;31(22):7819-7822.
doi: 10.1021/om300744m. Epub 2012 Aug 27.

Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination

Benjamin W Turnpenny  1 , Kiante L Hyman, Sherry R Chemler
Affiliations

Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination

Benjamin W Turnpenny et al. Organometallics. .

Abstract

An enantioselective copper-catalyzed hydroamination / cyclization of N-sulfonyl-2-allylanilines for the synthesis of chiral 2-methylindolines is reported. Chiral 2-methylindolines are important subunits in drugs and bioactive compounds. This method provides chiral N-sulfonyl-2-methyl indolines in up to 90% ee.

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Figures

Figure 1
Figure 1
Bioactive compounds containing the 2-methylindoline core
Figure 2
Figure 2
Carboamination side products
Scheme 1
Scheme 1
Proposed copper-catalyzed enantioselective hydroamination
Scheme 2
Scheme 2
Scope of the Enantioselective Indoline Synthesis
See this image and copyright information in PMC

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