A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.
A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.
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DOI：
10.1016/j.tetlet.2015.01.140
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发表时间：
2015-03-04
影响因子：
1.8
通讯作者：
Lindsley CW
中科院分区：
文献类型：
--
作者：
Senter TJ;O'Reilly MC;Chong KM;Sulikowski GA;Lindsley CW
采用对映选择性α-氯化法制备了c2功能化的氮杂啶和n -烷基端氮杂啶。该方法可快速制备功能化氮杂环，总产率为50-73%，ee为88-94%；氮杂环，总产率为22-32%，ee为84-92%。此外，我们开发了一种可扩展且具有成本效益的关键有机催化剂路线（总收率为54%，收率为95%）。
A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50–73% overall yields and 88–94% ee, and azetidines in 22–32% overall yields and 84–92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).