A catalytic and iterative route to beta-substituted esters via highly enantioselective conjugate addition of dimethylzinc to unsaturated malonates.
Using the chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition of dimethylzinc to acyclic unsaturated malonates, enantioselectivities of up to 98% have been obtained for the first time. An iterative and stereodivergent route to 3,5-dimethyl esters that takes advantage of this asymmetric catalysis has been developed.
Schuppan
Julia
J
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9749 AG Groningen, The Netherlands.
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007202:Indicators and Reagents; D008024:Ligands; D008314:Malonates / Q000737:chemistry*; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000475:Alkenes; D004952:Esters; D007202:Indicators and Reagents; D008024:Ligands; D008314:Malonates; D009943:Organophosphorus Compounds; D014297:Trimethylsilyl Compounds; C434331:phosphoramidite