CHIRAL BENZOQUINONES AS A NEW CLASS OF LIGANDS FOR ASYMMETRIC CATALYSIS : SYNTHESIS AND APPLICATION TO THE PALLADIUM(II)-CATALYZED 1,4-DIALKOXYLATION OF 1,3-DIENES
作者： Kenichiro Itami , Andreas Palmgren , Atli Thorarensen , Jan-E. Bäckvall
DOI: 10.1021/JO980561X
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摘要: Chiral C2-symmetric 2,5-bisamide hydroquinone ligands, with β-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate potential asymmetric induction utilizing benzoquinones palladium(II) catalysis, albeit modest enantiomeric excesses. Weakly coordinating hydroxyl groups ligand appear be crucial for success reaction. Mechanistic aspects and origin enantioselectivity are also discussed.
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