手性双环内酰胺的分子内烯反应
Intramolecular ene reaction of a chiral bicyclic lactam.
作者信息
Resek James E
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80503, USA.
出版信息
J Org Chem. 2008 Dec 19;73(24):9792-4. doi: 10.1021/jo801696r.
Abstract
The preparation of bicylic lactam 2 is described, employing an acetoacetate-based synthesis of 1,4-ketoacid 3. The lactam 2 was shown to undergo a thermal ene reaction at 280-300 degrees C to afford tricycle 7. Reduction of the ene product followed by removal of the chiral auxiliary fragment provided the unusual lactam system 9 in highly enantioenriched form.
摘要
描述了双环内酰胺2的制备方法，采用基于乙酰乙酸酯的1,4-酮酸3的合成方法。内酰胺2在280-300℃下发生热烯反应，生成三环化合物7。烯反应产物经还原，然后去除手性辅助片段，得到高度对映体富集形式的异常内酰胺体系9。
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本文引用的文献
1
An Asymmetric Route to Novel Chiral Cyclohexenones with Spiro-Connected Cyclopentenes. Further Utility of Chiral Bicyclic Thiolactams and the [3,3] Thio-Claisen Products.一条通往具有螺环连接环戊烯的新型手性环己烯酮的不对称路线。手性双环硫代内酰胺和[3,3]硫代克莱森产物的进一步应用。
J Org Chem. 1999 May 14;64(10):3585-3591. doi: 10.1021/jo982426q.
2
Asymmetric synthesis of 2-alkyl-perhydroazepines from [5,3,0]-bicyclic lactams.
J Org Chem. 2001 Feb 23;66(4):1413-9. doi: 10.1021/jo001548r.
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