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. 2009 Jul 29;131(29):9900-1.
doi: 10.1021/ja903880q.

Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand

Alexander M Taylor  1 , Ryan A Altman, Stephen L Buchwald
Affiliations

Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand

Alexander M Taylor et al. J Am Chem Soc. .

Abstract

The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess, and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.

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Figures

Figure 1
Figure 1
Pd-catalyzed enantioselective α-arylation of 1,3-dimethyl oxindole with an axially-chiral, P-chirogenic ligand.
Figure 2
Figure 2. Reactions to form other substituted oxindoles.a
aReactions were run at 50 °C using the same conditions as shown for Table 1. Results shown are the average of two runs. bYields of isolated material. cEnantiomeric excesses determined by chiral HPLC.
Scheme 1
Scheme 1
Derivatization of α-aryl and α-vinyl oxindole products.
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