Synthesis of Benzocycloheptanones through Coupling of δ,ε-Unsaturated Chromium Carbene Complexes and 2-Alkynylbenzoyl Derivatives

被引:9
|
作者
Patti, Rajesh Kumar [1 ]
Waynant, Kristopher V. [1 ]
Herndon, James W. [1 ]
机构
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
关键词
CYCLOADDITION CHEMISTRY; PRODUCT DISTRIBUTION; POTENT ANTAGONISTS; CHIRAL AUXILIARY; CYCLIZATION; RECEPTORS; ALDEHYDES; RHENIUM; SYSTEMS;
D O I
10.1021/ol200825j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling of pentenylcarbene complexes and 2-alkynylbenzoyl derivatives affords naphthocycloheptanones in a single step involving simultaneous construction of both the seven-membered ring and one of the aromatic rings. Aryl tethered systems undergo intramolecular cyclopropanation.
引用
收藏
页码:2848 / 2851
页数:4
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