期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 25, 页码 6669-6683出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600225
关键词
allylic substitution; asymmetric synthesis; Grignard reagents; organocopper reagents; synthetic methods
The ortho-diphenylphosphanylbenzoyl (o-DPPB) group was explored as a directing leaving group in copper-mediated and copper-catalyzed allylic substitution with Grignard reagents. Complete control of chemo-, regio- and stereoselectivity with complete syn-1,3-chirality transfer was observed as a result of the directed nature of the reaction. No excess of organometallic reagent is required and the directing group can be recovered quantitatively. Coordination studies in the solid state and in solution have shown that two substrates are bound via the phosphine function of the directing group at copper. Dynamic NMR experiments in solution are in agreement with a ligand-exchange process at copper, a prerequisite for the development of a substoichiometric process.
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