Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
J Org Chem. 2010 Nov 5;75(21):7061-72. doi: 10.1021/jo101680f.
Addition of α-arylmethylidene- or α-alkylidene-β-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.
通过亚胺醇醛途径将α-芳基甲基-或α-亚烷基-β-酮酯烯醇盐加成到 N-活化的亚胺,然后以级联方式进行分子内氮杂迈克尔反应,开发了一种高度非对映选择性的取代哌啶合成方法。从手性亚砜亚胺合成了对映纯哌啶。通过机理和计算研究对产物的形成和观察到的立体选择性进行了合理化。