Synfacts 2011(5): 0505-0505  
DOI: 10.1055/s-0030-1259873
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Calcium-Catalyzed Asymmetric Benzoyloxylation of 3-Aryloxindoles

Contributor(s): Hisashi Yamamoto, Jiajing Tan
Z. Zhang, W. Zheng, J. C. Antilla*
University of South Florida, Tampa, USA
Further Information

Publication History

Publication Date:
15 April 2011 (online)

Significance

The authors describe an asymmetric benzoyloxylation of 3-aryl-2-oxindoles in the presence of a chiral VAPOL calcium phosphate salt. The 3-hydroxy-2-oxindole products bearing quaternary stereogenic centers can be obtained with excellent enantioselectivities and yields. A similar calcium catalyst was reported by Ishihara’s group (Hatano et al. Angew. Chem. Int. Ed. 2010, 49, 3823), and this type of calcium phosphate salt chemistry has become an important addition to metal salt chemistry.