Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

被引：62
作者：
Dudnik, Alexander S. [1 ]
Schwier, Todd [1 ]
Gevorgyan, Vladimir [1 ]
机构：
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
来源：
TETRAHEDRON | 2009年 / 65卷 / 09期
基金：
美国国家卫生研究院;
关键词：
Gold; Propargylic esters; 1,3-Dienes; Naphthalenes; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; PROPARGYLIC ESTERS; ACYL MIGRATION; RING EXPANSION; GOLD CATALYSIS; ACCESS; REARRANGEMENT; KETONES; CYCLOISOMERIZATION;
D O I：
10.1016/j.tet.2008.10.109
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically Substituted naphthalenes has been developed. This domino process involves ail unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1859 / 1870
页数：12
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