Gold-catalyzed oxidative cyclizations on 1,4-enynes: Evidence for a γ-substituent effect on Wagner-Meerwein rearrangements

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Abstract

Gold-catalyzed oxidative cyclizations of 1,4-enynes were used to study the γ-effect on the Wagner-Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the γ-position can direct a stereospecific 1,2-shift of the anti-β-substituent regardless of its intrinsic properties. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Ghorpade, S., Su, M. D., & Liu, R. S. (2013). Gold-catalyzed oxidative cyclizations on 1,4-enynes: Evidence for a γ-substituent effect on Wagner-Meerwein rearrangements. Angewandte Chemie - International Edition, 52(15), 4229–4234. https://doi.org/10.1002/anie.201210313

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