Premium
3‐Spirocyclopropanedihydro‐ and ‐tetrahydropyridin‐4‐ones from Nitrone Cycloadducts of Bicyclopropylidene via 1‐(1′‐Aminomethylcyclopropyl)cyclopropanol under Pd II Catalysis
Author(s) -
Revuelta Julia,
Cicchi Stefano,
de Meijere Armin,
Brandi Alberto
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700912
Subject(s) - nitrone , chemistry , cycloaddition , ring (chemistry) , catalysis , medicinal chemistry , stereochemistry , organic chemistry
Abstract A series of 3‐spirocyclopropanedihydro‐ and ‐tetrahydropyrid‐4‐ones have been synthesized by nitrone cycloaddition to 1,1′‐bicyclopropylidene (BCP), chemoselective reduction of the N–O bond of the isoxazolidine ring, and Pd II ‐catalyzed cascade rearrangement of the β‐aminocyclopropanol derivatives into the final products. The new tetrahydropyridone derivatives were also prepared by thermal rearrangement of the isoxazolidines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)