Synthetic study demonstrates enantioselective aryloxylation of 3-bromooxindoles using cinchona catalysts, suggesting efficient access to complex bioactive alkaloid cores.
In this communication, the development of a highly enantioselective stereoablative protocol for the chemoselective aryloxylation of 3‐bromooxindoles with aryl alcohols have been realized. Promoted by easily available cinchona alkaloid derivatives (C6′−OH) under air‐ and moisture‐tolerant conditions, aryloxylation of a wide range of 3‐bromooxindoles bearing a 3′‐alkyl substituent proceeded in high yields and excellent enantioselectivities (up to 95% ee). The newly developed strategy expediently provided the 3‐phenoxy analogue of the core of alkaloid CPC‐1. magnified image
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Jadhav et al. (2017) studied this question.
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