Chiral N-phosphonyl imine chemistry:: Asymmetric addition of ketone-derived enolates for the synthesis of β-amino ketones
Chiral N-phosphonyl imine chemistry:: Asymmetric addition of ketone-derived enolates for the synthesis of β-amino ketones
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DOI：
10.1055/s-2008-1067189
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发表时间：
2008-08-01
影响因子：
2.6
通讯作者：
Li, Guigen
中科院分区：
文献类型：
--
作者：
Han, Jianlin;Ai, Teng;Li, Guigen
在方便的反应条件下，以高产率合成了新的手性N-膦酰亚胺。这些手性N-膦酰亚胺可以作为高效的亲电试剂与烯醇化锂酮进行不对称加成反应。对于十二个实施例，获得了良好的化学产率和优异的非对映选择性。发现手性助剂的N-1-萘基基团在控制该反应的非对映选择性方面上级优于其苄基对应物。在室温下，用HBr水溶液在甲醇中处理，可以很容易地除去手性助剂，以高产率得到游离的β-氨基酮。
New chiral N-phosphonyl imines have been synthesized in good yields under convenient reaction conditions. These chiral N-phosphonyl imines can serve as efficient electrophiles for asymmetric addition reactions with lithium ketone enolates. Good chemical yields and excellent diastereoselectivities were obtained for twelve examples. The N-1-naphthyl group of the chiral auxiliary was found to be superior to its benzyl counterpart in controlling the diastereoselectivity for this reaction. The chiral auxiliary can be readily removed by treatment with aqueous HBr in methanol at room temperature to give free beta-amino ketones in high yields.