Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones
Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones
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DOI：
10.1021/jo0511602
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发表时间：
2005-09-02
影响因子：
3.6
通讯作者：
Carretero, JC
中科院分区：
文献类型：
--
作者：
Esquivias, J;Arrayás, RG;Carretero, JC
对映体选择性催化1，4-加成到α，β-不饱和酮亚胺是前所未有的过程。在此，我们记录了铜催化的二烷基锌试剂加成到查尔酮的（2-吡啶磺酰基）亚胺上。该过程在手性亚磷酰胺配体的存在下快速发生，仅提供1，4-加成产物。在添加二甲基锌的情况下，获得70- 80%ee范围内的对映选择性。金属配位的2-吡啶基磺酰基的存在被证明是该反应进行所必需的
The enantios elective catalytic 1,4-addition to alpha,beta-unsaturated ketimines is an unprecedented process. Herein, we document the copper-catalyzed addition of dialkylzinc reagents to (2-pyridylsulfonyl)imines of chalcones. This process occurs rapidly in the presence of a chiral phosphoramidite ligand to afford exclusively the 1,4-addition product. In the case of addition of dimethylzinc, enantioselectivities in the range 70-80% ee are obtained. The presence of the metalcoordinating 2-pyridylsulfonyl group proved to be essential for this reaction to proceed