Overturning indolyne regioselectivities and synthesis of indolactam V

SM Bronner, AE Goetz, NK Garg

Index: Bronner, Sarah M.; Goetz, Adam E.; Garg, Neil K. Journal of the American Chemical Society, 2011 , vol. 133, # 11 p. 3832 - 3835

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Citation Number: 73

Abstract

We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4, 5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an ...