A Mild Method for the Generation and Interception of 1,2-Cycloheptadienes with 1,3-Dipoles

被引：20
|
作者：
Almehmadi, Yaseen A. [1 ,2 ]
West, F. G. [1 ]
机构：
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
[2] King Abdulaziz Univ, Dept Chem, Coll Sci & Arts, Rabigh 21911, Saudi Arabia
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 15期
基金：
加拿大自然科学与工程研究理事会;
关键词：
STRAINED ALLENES; ARYNE CHEMISTRY; CYCLOHEXA-1,2-DIENE; CYCLOADDITIONS; SUBSTITUTION; BENZYNES; AMINES;
D O I：
10.1021/acs.orglett.0c02172
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,2-Cycloheptadiene is a strained, transient species that has been underutilized as a synthetic building block. Seven-membered cyclic allenes are mostly known for their propensity to undergo rapid dimerization, and relatively little has been reported regarding their cycloaddition reactivity with 1,3-dienes or 1,3-dipoles. This work describes the trapping of 1-acetoxy-1,2-cycloheptadiene and its unsubstituted counterpart, generated via desilylative elimination, with a range of 1,3-dipolar trapping partners, affording complex polycyclic products with high regio- and diastereoselectivity.
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页码：6091 / 6095
页数：5
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