期刊
TETRAHEDRON LETTERS
卷 49, 期 18, 页码 2985-2989出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.02.175
关键词
asymmetric catalyst; imidazolium; homoenolate; N-heterocyclic carbene; umpolung
A N(1)-C(5) bridged chiral bicyclic imidazole with a morpholine framework was synthesized from an enantiopure 2-amino alcohol. The resultant imidazole reacted with various electrophiles, including primary and secondary alkyl halides, benzyne, and an electron-deficient aryl halide, to give the corresponding imidazolium salts. Some of the imidazolium salts were found to have potential as the precursor of a chiral N-heterocyclic carbene catalyst; by the direct annulation of an enal and a ketone through the intermediacy of a homoenolate and an activated carboxylate, the target lactone was obtained in an enantiomerically enriched form (up to 66% ee). (C) 2008 Elsevier Ltd. All rights reserved.
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