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From Amino Acids to Enantiopure Bicyclic Isoxazolidinylpyridin‐4(1 H )‐ones through Intramolecular Nitrone Cycloadditions
Author(s) -
Romeo Roberto,
Iannazzo Daniela,
Piperno Anna,
Chiacchio Maria A.,
Corsaro Antonino,
Rescifina Antonio
Publication year - 2005
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.200400847
Subject(s) - enantiopure drug , chemistry , bicyclic molecule , nitrone , intramolecular force , cycloaddition , stereochemistry , substrate (aquarium) , amino acid , enantioselective synthesis , organic chemistry , catalysis , geology , oceanography , biochemistry
Homochiral bicyclic isoxazolidinylpyridin‐4(1 H )‐ones have been synthesised by an intramolecular nitrone cycloaddition process, starting from homochiral β‐amino acids. Stereoselection at C 2 or C 3 of the acyclic substrate appears to give the best results in the control of the stereochemistry of the new formed chiral centres. The synthetic approach has been further directed towards functionalised piperidones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)