503004-87-3Relevant academic research and scientific papers
Perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as ligands for the catalytic enantioselective addition of diethylzinc to aldehydes
Andres, Celia,Infante, Rebeca,Nieto, Javier
, p. 2230 - 2237 (2010)
The catalytic potency of a series of perhydro-1,3-benzoxazines prepared from (-)-8-aminomenthol was examined in the enantioselective addition of diethylzinc to aldehydes. When (2R,3S,3aS,4aR,6R,8aS)-2-isopropyl-6,9,9- trimethyl-3-phenyldecahydro-4aH-pyrrolo[2,1-b][1,3]benzoxazin-3-ol 7b was used as a chiral ligand, 1-substituted propanols with an (R)-configuration were obtained in high yields and enantiomeric excesses up to >99%. The catalyst can be recovered and used without any loss in its activity.
Enantioselective addition of dimethylzinc to aldehydes catalyzed by a chiral perhydro-1,3-benzoxazine-based amino alcohol as ligand
Infante, Rebeca,Nieto, Javier,Andrs, Celia
supporting information; experimental part, p. 1343 - 1348 (2012/06/30)
Dimethylzinc undergoes efficient enantioselective addition to a wide variety of aromatic and aliphatic aldehydes in the presence of a catalytic amount of a chiral perhydro-1,3-benzoxazine-based amino alcohol. Methyl carbinols are obtained in good yields and in enantiomeric excesses of 99% or more in the absence of any metal other than zinc. Georg Thieme Verlag Stuttgart · New York.
Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations
Pedrosa, Rafael,Andres, Celia,Roson, Carlos D.,Vicente, Martina
, p. 1852 - 1858 (2007/10/03)
Reaction conditions determine the stereoselection in the intramolecular keto-ene reaction. The thermolysis of chiral 2-acyl-3-allyl-substituted 1,3-perhydrobenzoxazines derived from (-)-8-aminomenthol gives a mixture of only two cis-3-hydroxy-3,4-disubstituted pyrrolidine nuclei. The stereochemistry of the major diastereoisomer depends on both the temperature and the reaction time.
