350508-53-1Relevant 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
experimental part, p. 2230 - 2237 (2010/11/04)
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.
1,4-Asymmetric induction in methoxyselenenylation of double bonds at the nitrogen side of chiral perhydro-1,3-benzoxazines promoted by nonbonded Se...N interactions
Pedrosa, Rafael,Andres, Celia,Mendiguchia, Pilar,Nieto, Javier
, p. 5388 - 5391 (2007/10/03)
Regio- and diastereoselective methoxyselenenylation of cinnamylamines attached to a chiral perhydrobenzoxazine occurs in high yields by reaction with benzeneselenenyl chloride in dichloromethane-methanol. The diastereoselection is dependent on the tempera
Synthesis of enantiopure mono- and disubstituted tetrahydroisoquinolines by 6-exo radical cyclizations
Pedrosa, Rafael,Andrés, Celia,Iglesias, Jesús M,Obeso, Manuel A
, p. 4005 - 4014 (2007/10/03)
2-(o-Bromophenyl)-3-allyl- and 2-allyl-3-(o-bromobenzyl)-substituted perhydrobenzoxazines, derived from (-)-8-amino menthol, readily cyclized stereoselectively by reaction with tributyltin hydride in the presence of AIBN. The cyclization compounds were transformed into enantiopure 4-alkyl tetrahydroisoquinolines by reductive ring opening of the N,O-acetal moiety with lithium aluminum hydride. Enantiopure 1,4- and 3,4-dialkyl-substituted tetrahydroisoquinolines were also prepared by reaction of the cyclized compounds with methylmagnesium iodide and subsequent elimination of the menthol appendage.
