Gold-Catalyzed Oxidative Cyclizations on 1,4-Enynes: Evidence for a γ-Substituent Effect on Wagner-Meerwein Rearrangements

Gold-Catalyzed Oxidative Cyclizations on 1,4-Enynes: Evidence for a γ-Substituent Effect on Wagner-Meerwein Rearrangements

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 intrin...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-04, Vol.52 (15), p.4229-4234
Hauptverfasser: Ghorpade, Satish, Su, Ming-Der, Liu, Rai-Shung
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
carbenes
Catalysis
Cyclization
gold
homogeneous catalysis
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Organogold Compounds - chemistry
Oxidation-Reduction
Stereoisomerism
Wagner-Meerwein rearrangement
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201210313