Modular ligands derived from amino acids for the enantioselective addition of organozinc reagents to aldehydes.
A new series of modular chiral ligands that are derived from amino acids were prepared and tested for their ability to catalyze the asymmetric addition of alkylzinc reagents to aromatic and aliphatic aldehydes. The ligands contain a tertiary amine, an amino acid side chain, and a carbamate or amide functional group. One ligand, which was synthesized from Ile, catalyzes the addition of diethylzinc to cyclohexanecarboxaldehyde in 99% ee.
Richmond
Meaghan L
ML
Department of Chemistry, Brown University, 324 Brook Street, Box H, Providence, Rhode Island 02912, USA.
Seto
Christopher T
CT
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D008024:Ligands; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc
D000447:Aldehydes; D000596:Amino Acids; D008024:Ligands; D009942:Organometallic Compounds; D015032:Zinc