N-杂环卡宾和布朗斯特酸协同催化：反式γ-内酰胺的不对称合成。
N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
出版信息
J Am Chem Soc. 2011 Aug 17;133(32):12466-9. doi: 10.1021/ja205714g. Epub 2011 Jul 25.
Abstract
An efficient enantioselective approach to form trans-γ-lactams in up to 99% yield, 93% ee, and >20/1 dr using unactivated imines has been developed. The cyclohexyl-substituted azolium and the weak base sodium o-chlorobenzoate are most suitable for this transformation. Notably, the process involves cooperative catalysis by an N-heterocyclic carbene and a Brønsted acid.
摘要
已开发出一种高效的对映选择性方法，可使用未活化的亚胺以高达 99%的收率、93%的对映体过量和>20/1 的 dr 形成反式-γ-内酰胺。环己基取代的唑鎓盐和弱碱邻氯苯甲酸钠对这种转化最适用。值得注意的是，该过程涉及 N-杂环卡宾和布朗斯台德酸的协同催化。
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