路易斯酸催化的活化氮丙啶与烯醇化物的高立体选择性的多米诺环开环环化反应：功能化手性γ-内酰胺的合成。
Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams.
机构信息
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
出版信息
J Org Chem. 2010 Sep 17;75(18):6173-81. doi: 10.1021/jo101004x.
PMID:20707384
Abstract
A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral γ-lactams in a domino fashion has been developed. γ-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.
摘要
已开发出一种高对映选择性和非对映选择性路易斯酸催化的 S(N)2 型环开环，随后与活泼亚甲基碳亲核试剂进行环化反应，以顺式方式构建功能化的手性 γ-内酰胺的多米诺反应。γ-内酰胺进行脱磺化和脱羧反应，分别以良好的产率提供吡咯烷酮-3-羧酸酯和 N-对甲苯磺酰基吡咯烷酮衍生物。
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