An asymmetric reductive aldol-type reaction of α,β-unsaturated esters with carbonyl compounds using Rh catalyst and Et 2 Zn was investigated. A chiral zinc complex from α,β-unsaturated ester was easily generated as the key intermediate from Et 2 Zn and Wilkinson's catalyst with diisopropyl L-( )-tartrate to give a variety of enantioenriched β-hydroxy esters. The reaction was also applied to the intramolecular reductive aldol cyclization.
Dialkyl Tartrate as a Chiral Ligand. -(R,R)-Diisopropyl tartrate is used as a source of chirality in the inter-or intramolecular reductive aldol-type synthesis of -hydroxy esters, however, the chiral induction is rather poor. -(ISODA, M.; SATO, K.; TOKURA, Y.; TARUI, A.; OMOTE, M.; ANDO*, A.; Chem. Pharm. Bull. 62 (2014) 10, 956-961, http://dx.doi.org/10.1248/cpb.c14-00223 ; Fac. Pharm. Sci., Setsunan Univ., Hirakata, Osaka 573-0101, Japan; Eng.) -R. Staver 13-030
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