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

被引：77
作者：
Ghorpade, Satish [1 ]
Su, Ming-Der [2 ]
Liu, Rai-Shung [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
[2] Natl Chiayi Univ, Dept Appl Chem, Chiayi 60004, Taiwan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 15期
关键词：
carbenes; cyclization; gold; homogeneous catalysis; WagnerMeerwein rearrangement; AB-INITIO; RING EXPANSIONS; EFFICIENT; MOLECULES; ALKYNYLCYCLOPROPANES; CYCLOISOMERIZATION; POTENTIALS; DIVERSITY; MECHANISM; MIGRATION;
D O I：
10.1002/anie.201210313
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：4229 / 4234
页数：6
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