Journal
TETRAHEDRON
Volume 56, Issue 18, Pages 2865-2878Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00142-3
Keywords
phosphoramidite ligand; copper; enantioselective conjugate addition; enones; non-linear effect; diethyl zinc; catalytic 1,4-addition
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A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.'s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones. (C) 2000 Elsevier Science Ltd. All rights reserved.
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