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Reaction Pathways through a [1,5]‐Hydride Shift Triggered by Acids: Approach to Bridged‐Ring Heterocycles and Polycycles
Author(s) -
Zhen Le,
Dai Liang,
Yu ShengQi,
Lin Chao,
Sun Hongbin,
Xu QingLong
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601319
Subject(s) - chemistry , hydride , ring (chemistry) , combinatorial chemistry , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , hydrogen
The [1,5]‐hydride shift/cyclization process as a new C sp³ –H bond functionalization has made tremendous advances over the past decades. Herein, we describe reaction pathways for a [1,5]‐hydride shift that is triggered by acid. In these transformations, the diene isoindoles are generated in situ and undergo a reaction with different dienophiles to provide access to a series of bridged‐ring heterocycles and polycycles in good yields (up to 94 %). In addition, we found that the choice of acid played a critical role and could be used to control the structure of the final product.