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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Published inAngewandte Chemie International Edition Vol. 52; no. 15; pp. 4229 - 4234
Main Authors Ghorpade, Satish, Su, Ming-Der, Liu, Rai-Shung
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.04.2013
WILEY‐VCH Verlag
Wiley
Subjects
Alkynes - chemistry
carbenes
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
gold
homogeneous catalysis
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Organogold Compounds - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
Wagner-Meerwein rearrangement
MIGRATION
RING EXPANSIONS
MECHANISM
AB-INITIO
carbenes
WagnerMeerwein rearrangement
ALKYNYLCYCLOPROPANES
POTENTIALS
cyclization
MOLECULES
gold
homogeneous catalysis
CYCLOISOMERIZATION
DIVERSITY
EFFICIENT
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Summary: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.
Bibliography:istex:228B9207075F34D29D6FCCE7C55AF912A2D6A465
National Science Council, Taiwan
ark:/67375/WNG-ST5LG6VW-C
ArticleID:ANIE201210313
We thank National Science Council, Taiwan, for financial support of this work.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201210313