Sequential Diels-Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration
Sequential Diels-Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration
复制标题
连续 Diels-Alder 反应/重排序列：功能化双环[2.2.1]庚烷衍生物的合成及其相对构型的修改
DOI：
10.1021/jo500942a
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发表时间：
2014-07-18
影响因子：
3.6
通讯作者：
Goeke, Andreas
中科院分区：
文献类型：
--
作者：
Liang, Demin;Zou, Yue;Goeke, Andreas
发展了一种连续的Diels-Alder反应/重排序列用于合成作为新型花和木香味剂的多种官能化双环[2.2.1]庚烷。重排的结果取决于二烯的取代模式。2D NMR分析已经建立了双环[2.2.1]庚酮的正确相对构型，其最初被错误分配。此外，当引发DA反应由手性刘易斯酸催化时，可以以高达96.5：3.5的对映体比（er）获得包括（+）-herbanone的双环[2.2.1]庚烷衍生物。
A sequential Diels-Alder reaction/rearrangement sequence was developed for the synthesis of diverse fimctionalized bicyclo[2.2.1]heptanes as novel floral and woody odorants. The outcome of the rearrangement depended on the substitution pattern of the dienes. 2D NMR analysis has established the correct relative configuration of the bicyclo[2.2.1]heptanone, which was originally misassigned. Furthermore, when the initiating DA reaction was catalyzed by a chiral Lewis acid, the bicyclo[2.2.1]heptane derivatives including (+)-herbanone can be obtained in an enantiomeric ratio (er) up to 96.5:3.5.