HIGHLY DIASTEREOSELECTIVE COUPLING REACTIONS BETWEEN CHIRAL BENZALDEHYDE TRICARBONYLCHROMIUM COMPLEXES AND ACTIVATED DOUBLE-BONDS
HIGHLY DIASTEREOSELECTIVE COUPLING REACTIONS BETWEEN CHIRAL BENZALDEHYDE TRICARBONYLCHROMIUM COMPLEXES AND ACTIVATED DOUBLE-BONDS
复制标题
DOI：
10.1016/s0040-4039(00)61594-0
复制
发表时间：
1993-10-29
影响因子：
1.8
通讯作者：
BERNARDINELLI, G
中科院分区：
文献类型：
--
作者：
KUNDIG, EP;XU, LH;BERNARDINELLI, G
当芳烃与亲电基团Cr（CO）3络合时，胺催化的丙烯酸衍生物与苯甲醛的偶联反应（Baylis-Hillman反应）更有效。与平面手性邻位取代苯甲醛配合物的反应具有高度的非对映选择性。3-羟基-2-亚甲基链烷酸衍生物可以从容易获得的对映体纯的络合物有效地获得并且具有非常高的对映体过量。在一种情况下，通过X-射线结构分析确定了相对于芳烃络合物的平面手性的苄基立体中心的构型。该反应已扩展到邻茴香醚亚胺络合物。
The amine catalyzed coupling reaction of acrylic derivatives with benzaldehydes (Baylis-Hillman reaction) is more efficient when the arene is complexed to the electrophilic Cr(CO)3 group. Reactions with planar chiral o-substituted benzaldehyde complexes are highly diastereoselective. 3-Hydroxy-2-methylenealkanoic acid derivatives can be obtained efficiently and with very high enantiomeric excess from readily accessible enantiomerically pure complexes. The configuration of the benzylic stereogenic center relative to the planar chirality of the arene complex was determined in one case by an X-ray structural analysis. The reaction has been extended to an o-anisaldehydeimine complex.