Peer-Reviewed Journal Details
Mandatory Fields
Doyle, L;Heaney, F
2011
March
Tetrahedron
NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis
Published
6 ()
Optional Fields
DIELS-ALDER REACTIONS IMINIUM ION CATALYSIS CYCLOADDITION REACTIONS CHIRAL AUXILIARIES ENAMINE CATALYSIS STRATEGY NITRONES ACCELERATION GENERATION DESIGN
67
2132
2138
A new scaffold for organocatalysis of the Diels-Alder reaction is disclosed; an isoxazolidine ring forms the core of the catalyst and its activity is enhanced by judicious fusion of a second five-membered heterocycle to the c-edge. The catalyst performance is improved by the incorporation of an endo-cyclic electron withdrawing group adjacent to the fusion point. The organic core is effective only in the presence of an acid co-catalyst and whilst the two-component system shows potential as an enantioselective catalyst it is demonstrated that stereocontrol is a feature of the organic core and is fully independent of the choice of co-catalyst. (C) 2011 Elsevier Ltd. All rights reserved.
OXFORD
0040-4020
10.1016/j.tet.2011.01.034
Grant Details