2-(aminomethyl)-oxazolines: highly modular scaffolds for the preparation of novel asymmetric ligands.
Highly modular chiral 2-(aminoalkyl)oxazolines have been prepared from alpha-amino acids and 1,2-amino alcohols. The amine-functionalized oxazolines were employed as scaffolds in the preparation of a number of different ligands with potential denticities varying from 2 to 5. The obtained ligands were employed and evaluated in the ruthenium-catalyzed asymmetric transfer-hydrogenation of acetophenone and in the titanium-catalyzed addition of diethylzinc to aldehydes. In the latter process, enantioselectivity up to 97% was obtained.
Västilä
Patrik
P
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
Pastor
Isidro M
IM
Adolfsson
Hans
H
D000596:Amino Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
D000596:Amino Acids; D000605:Amino Alcohols; D007202:Indicators and Reagents; D010080:Oxazoles; D012428:Ruthenium; D014025:Titanium; D015032:Zinc