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2005
Carboxylic acid esters
Q 0530
Rhodium Catalyzed Tandem Conjugate Addition-Protonation: An EnantioselecSynthesis of 2-Substituted Succinic Esters. — Addition of potassium trifluo05- 080 tive
ro(organo)borate salts (II) to dimethyl itaconate (I) leads to formation of an intermediate complex which on protonation furnishes enantioenriched succinic esters (III). Additional chiral ligand is essential to achieve good asymmetric induction as well as high
temperature for enantioselectivity. Noteworthy, addition of alkenes, e.g. (IIa), yields
products which are not accessible by approaches involving enantioselective hydrogenation. — (MOSS, R. J.; WADSWORTH, K. J.; CHAPMAN, C. J.; FROST*, C. G.;
Chem. Commun. (Cambridge) 2004, 17, 1984-1985; Dep. Chem., Univ. Bath,
Claverton Down, Bath BA2 7AY, UK; Eng.) — H. Hoennerscheid
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