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Palladium‐catalyzed selective alkoxycarbonylation of N ‐vinylphthalimide
Author(s) -
Zhu Bing Chun,
Jiang Xuan Zhen
Publication year - 2006
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1046
Subject(s) - chemistry , palladium , regioselectivity , catalysis , phosphine , substrate (aquarium) , yield (engineering) , ligand (biochemistry) , organic chemistry , carbonylation , combinatorial chemistry , medicinal chemistry , biochemistry , oceanography , materials science , receptor , carbon monoxide , metallurgy , geology
The palladium‐catalyzed selective alkoxycarbonylation of enamide was studied using N ‐vinylphthalimide as the model substrate. Both palladium (0) and palladium (II) compounds can be used as the catalyst precursors. It was found that the efficiency and the regioselectivity of the reaction depended remarkably on phosphine ligands and other reaction parameters such as solvent, substrate concentration, temperature and promoters. Good yields and high regioselectivities of either the branched or linear products were obtained under optimum reaction conditions. The primary optical yield (12.3%) of N ‐Phthaloyl‐ L ‐alanine methyl ester (2) was obtained using ( S )‐(+)‐BNPPA as the chiral ligand. A possible reaction mechanism for the alkoxycarbonylation of N ‐vinylphthalimide was also proposed. Copyright © 2006 John Wiley & Sons, Ltd.