通过氮杂环丙烷开环反应合成带有高度官能化2-烷基取代基的吡啶的不对称方法。
Asymmetric route to pyridines bearing a highly functionalized 2-alkyl substituent by aziridine ring-opening reactions.
作者信息
Savoia Diego, Alvaro Giuseppe, Di Fabio Romano, Gualandi Andrea
机构信息
Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, 40126 Bologna, Italy.
出版信息
J Org Chem. 2007 May 11;72(10):3859-62. doi: 10.1021/jo070364a. Epub 2007 Apr 14.
PMID:17432914
Abstract
The aziridine prepared from the 2-pyridineimine derived from (S)-valinol underwent ring-opening by attack of nitrogen, sulfur, and oxygen nucleophiles. Complete or prevalent regioselectivity was obtained using cerium trichloride heptahydrate as a catalyst. In some cases, the N-substituent could be removed by an oxidative protocol.
摘要
由(S)-缬氨醇衍生的2-吡啶亚胺制备的氮丙啶通过氮、硫和氧亲核试剂的进攻发生开环反应。使用七水合三氯化铈作为催化剂可获得完全或主要的区域选择性。在某些情况下，N-取代基可通过氧化方法除去。
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