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Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities
Author(s) -
Giorgi Gianluca,
Lampariello L. Raffaella,
Minetto Giacomo,
Paoli M. Laura,
Riello Vincenzo,
Rodriquez Manuela,
Sega Alessandro
Publication year - 2003
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.200300480
Subject(s) - bicyclic molecule , chemistry , regioselectivity , nitrile , cycloaddition , cyclopentene , 1,3 dipolar cycloaddition , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A completely regioselective approach to bicyclic isoxazolines has been found starting from 4‐cyclopentene‐1,3‐dione or 2‐cyclopentenones. 1,3‐Dipolar cycloaddition with nitrile oxides gave different semirigid bicyclic scaffolds with at least four points of elaboration for molecular diversity. From these intermediates, two families of regioisomer isoxazolines can be prepared with complete control of their relative stereochemistry. Further elaboration of functional groups was demonstrated in order to exploit a successive parallel preparation of arrays of compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)