Intramolecular Diels-Alder reactions. 5 - Facile synthesis of an octahydrobenzocycloheptenone derivative utilising intramolecular Diels-Alder reaction

被引：0

作者：

Frey, B ^{[1
]}

Reissig, HU ^{[1
]}

机构：

[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1999年 / 341卷 / 02期

关键词：

carbocycles; cycloadditions; Lewis acids; titanium; cycloheptanone;

D O I：

10.1002/(SICI)1521-3897(199902)341:2<173::AID-PRAC173>3.0.CO;2-M

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Undecatrienone 4 was prepared in a short sequence via siloxycyclopropanes 1 and 3. Intramolecular Diels-Alder reaction (IMDA) of 4 under various conditions afforded octahydrobenzocycloheptenone derivative 5 as a mixture of three or four diastereomers. High diastereoselectivities in favour of the endo-product cis-5a could be obtained with TiCl4 as promoter. This selectivities were attributed to the formation of a seven-membered ring chelate as intermediate. The configurational assignment of all four diastereomers of 5 was based on isomerisation reactions and NMR analysis.

引用

页码：173 / 178

页数：6

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