Nucleophilic Ring-Opening of Epoxide and Aziridine Acetates for the Stereodivergent Synthesis of β-Hydroxy and β-Amino γ-Lactams
Nucleophilic Ring-Opening of Epoxide and Aziridine Acetates for the Stereodivergent Synthesis of β-Hydroxy and β-Amino γ-Lactams
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DOI：
10.1021/jo102267h
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发表时间：
2011-02-04
影响因子：
3.6
通讯作者：
Sa, Marcus M.
中科院分区：
文献类型：
--
作者：
Bisol, Tula B.;Bortoluzzi, Adailton J.;Sa, Marcus M.
以易获得的环氧化物和叠氮吡啶醋酸酯为原料，合成了具有高度区域选择性和立体选择性的新型β， γ -二取代γ -内酰胺。关键步骤包括这些三元杂环的区域和非对映控制的亲核开环，然后是γ -氮基酯中间体的轻度还原环化。该方法还扩展到手性环氧乙酸酯不对称合成(4R,5S)-4-羟基-5-苯基吡咯烷酮-2- 1。这种多功能合成功能化γ -内酰胺的主要特点包括涉及廉价试剂和温和的条件以及高化学效率。
A highly regio- and stereoselective synthesis of novel beta,gamma-disubstituted gamma-lactams with either an anti or syn relative configuration was developed from readily available epoxide and aziridine acetates. The key steps include the regio- and diastereocontrolled nucleophilic ring-opening of these three-membered heterocycles followed by mild reductive cyclization of the gamma-azido ester intermediate. The method was also extended to an asymmetric synthesis of (4R,5S)-4-hydroxy-5-phenylpyrrolidin-2-one from a chiral epoxide acetate. The main features of this versatile synthesis of functionalized gamma-lactams include the involvement of inexpensive reagents and mild conditions together with high chemical efficiency.