Synfacts 2010(2): 0196-0196  
DOI: 10.1055/s-0029-1219146
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Conjugate Addition of 3-Substituted Oxindoles in Water-Rich Solvent

Contributor(s): Mark Lautens, Chit Tsui
R. He, S. Shirakawa, K. Maruoka*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
21 January 2010 (online)

Significance

The authors have developed an enantioselective conjugate addition of 3-arylox­indoles to β-nitrostyrene in the presence of the chiral phase-transfer catalyst (S)-1. Oxindoles are important building blocks in many alkaloids and pharmaceuticals. This highly efficient and selective method provides access to enantiomerically enriched adducts, which can be transformed into the core structure of alkaloids in a few steps with retention of the stereochemistry.