环丙烯亚胺催化的叔丁基甘氨酸酯与 N-Boc-亚胺的对映选择性 Mannich 反应。
Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.
机构信息
Department of Chemistry, Columbia University, New York, New York 10027, USA.
出版信息
J Am Chem Soc. 2013 Aug 14;135(32):11799-802. doi: 10.1021/ja407277a. Epub 2013 Aug 1.
Abstract
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol of product is shown using 1 mol % catalyst. The products of this transformation can be converted into several useful derivatives.
摘要
环丙烯亚胺 1 被证明可以在高对映选择性和非对映选择性条件下催化甘氨酸亚胺与 N-Boc-醛亚胺的曼尼希反应。1 的反应性明显大于广泛使用的硫脲金鸡纳生物碱衍生催化剂。各种芳基和脂肪族 N-Boc-醛亚胺都是这种转化的有效底物。使用 1 mol%的催化剂进行了制备规模的反应，以提供超过 90 mmol 的产物。该转化的产物可以转化为几种有用的衍生物。
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