New aniline-containing amino alcohols from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane as useful intermediates for the synthesis of chiral ligands, bases, and benzoxazine nucleus.
New enantiopure aniline-containing amino alcohols are directly derived from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane, by alternative regioselective double reductions. Subsequent selective alkylation procedures and derivatizations provide a rapid and high-yielding access to different chiral ligands, bases, and benzoxazines, without loss of optical purity.
Solladié-Cavallo
Arlette
A
Laboratoire de Stéréochimie Organométallique associé au CNRS, ECPM/Université L. Pasteur, 25 rue Becquerel, 67087 Strasbourg, France.
Lupattelli
Paolo
P
Bonini
Carlo
C
Ostuni
Valeria
V
Blasio
Nadia Di
ND
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D008024:Ligands; D008968:Molecular Conformation; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
C517338:2-(2-nitrophenyl)-3-phenyloxirane; D000605:Amino Alcohols; D000814:Aniline Compounds; D048588:Benzoxazines; D004852:Epoxy Compounds; D008024:Ligands; D013267:Stilbenes; C023650:aniline