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 in	Angewandte Chemie International Edition Vol. 52; no. 15; pp. 4229 - 4234
Main Authors	Ghorpade, Satish, Su, Ming-Der, Liu, Rai-Shung
Format	Journal Article
Language	English
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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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.
AbstractList	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.
Author	Liu, Rai-Shung Su, Ming-Der Ghorpade, Satish
Author_xml	– sequence: 1 givenname: Satish surname: Ghorpade fullname: Ghorpade, Satish organization: Department of Chemistry, National Tsing-Hua University, Hsinchu, 30043 (Taiwan, ROC) – sequence: 2 givenname: Ming-Der surname: Su fullname: Su, Ming-Der email: midesu@mail.ncyu.edu.tw organization: Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 (Taiwan, ROC) – sequence: 3 givenname: Rai-Shung surname: Liu fullname: Liu, Rai-Shung email: rsliu@mx.nthu.edu.tw organization: Department of Chemistry, National Tsing-Hua University, Hsinchu, 30043 (Taiwan, ROC)
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/23463682$$D View this record in MEDLINE/PubMed
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Keywords	MIGRATION RING EXPANSIONS MECHANISM AB-INITIO carbenes WagnerMeerwein rearrangement ALKYNYLCYCLOPROPANES POTENTIALS cyclization MOLECULES gold homogeneous catalysis CYCLOISOMERIZATION DIVERSITY EFFICIENT
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Snippet	Gold‐catalyzed oxidative cyclizations of 1,4‐enynes were used to study the γ‐effect on the Wagner–Meerwein rearrangement. Both experimental and theoretical...
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SubjectTerms	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
Title	Gold-Catalyzed Oxidative Cyclizations on 1,4-Enynes: Evidence for a γ-Substituent Effect on Wagner-Meerwein Rearrangements
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