Some new C2-symmetric bicyclo[2.2.1]heptadiene ligands: synthesis and catalytic activity in rhodium(I)-catalyzed asymmetric 1,4- and 1,2-additions
作者： Timothy Noël , Koen Vandyck , Johan Van der Eycken
DOI: 10.1016/J.TET.2007.10.034
关键词: Steric effects 、 Rhodium 、 Chemistry 、 Reactivity (chemistry) 、 Stereochemistry 、 Aryl 、 Bicyclic molecule 、 Phenylboronic acid 、 Medicinal chemistry 、 Selectivity 、 Catalysis
摘要: Abstract C2-Symmetric bicyclo[2.2.1]hepta-2,5-dienes with various substituents (R=Bn, i-Bu, c-Hex, allyl) are prepared starting from the corresponding enantiomerically pure bis-triflate (R=OTf). These chiral ligands tested and compared in rhodium(I)-catalyzed 1,4- 1,2-addition of phenylboronic acid to cyclic enones aryl aldehydes, respectively. Some interesting reactivity selectivity effects due introduction sterically demanding or olefinic reported. Moreover, remarkably high catalytic activity is observed for 1,2-addition.
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