Stereoselective Addition of Grignard Reagents to New P-Chirogenic N-Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity
Stereoselective Addition of Grignard Reagents to New P-Chirogenic N-Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity
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DOI：
10.1002/ejoc.201100380
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发表时间：
2011-07-01
影响因子：
2.8
通讯作者：
Colobert, Francoise
中科院分区：
文献类型：
--
作者：
Francesco, Irene Notar;Egloff, Coraline;Colobert, Francoise
以适当的氧化膦为起始原料，经五步反应合成了几种膦酰亚胺，然后与甲基溴化镁反应，得到了高产率和有希望的非对映异构体。然后将结果最好的N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine，与不同的格氏试剂进行1，2-加成反应，以评价立体生成的磷原子对手性诱导的最佳效果。以优异的产率和中等至优良的非对映异构体比率获得了相应的加合物。
Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios.