کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5230392 | 1383693 | 2007 | 11 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Synthesis of nitrogen-containing spirocyclic scaffolds via aminoallylation/RCM sequence Synthesis of nitrogen-containing spirocyclic scaffolds via aminoallylation/RCM sequence](/preview/png/5230392.png)
A concise route to nitrogen-containing spirocyclic scaffolds was developed. It is based on the allylation of imines derived from cyclic ketones. The resulting homoallylamines were subsequently alkylated with bromomethylmethacrylate resulting in propenyl-butenyl substituted amine derivatives. Basic amines such as 4 or 10 were cyclized with the Grubbs 2nd generation catalyst in the presence of pTsOH. Carbamate derivatives could be converted to tetrahydropiperidine derivatives with the same catalyst. It could be shown that the acrylate functionality can be degraded to the ketone using the classical sequence consisting of Curtius rearrangement of the derived acrylic acid followed by hydrolysis of the vinyl isocyanate. Other modifications include reduction of the acrylate double bond, saponification of the ester group, and amide formation.
Journal: Tetrahedron - Volume 63, Issue 42, 15 October 2007, Pages 10486-10496