期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 30, 页码 9215-9222出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800942
关键词
carbenes; chirality; cyclophanes; heterocycles; umpolung
Cyclophane-type imidazolium salts with planar chirality were synthesized from enantiopure 2-amino alcohols, of which the N(1) and N(3) positions were connected with a bridge. The structural profiles of the imidazolium salts and their derivative N-heterocyclic carbenes (NHCs) were investigated by means of several analyses. The chiral NHCs derived from these imidazolium salts were found to catalyze the asymmetric cross-annulation of an a,p-unsaturated aldehyde with a ketone by means of the conjugated umpolung of the enal to give the target gamma-lactone with good to excellent enantioselectivity (up to 94% ee). Based on the expected structure of the NHCs and their intermediates, together with the absolute configuration of the products, a plausible mechanism for the stereocontrol was proposed.
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