Rondot, ChristopheRetailleau, PascalZhu, Jieping2010-11-252010-11-252010-11-25200710.1021/ol0627202https://infoscience.epfl.ch/handle/20.500.14299/58428An efficient synthesis of chiral dihydrooxazines from 1-aryl-2-amino-propane-1,3-diols via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an SN1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irresp. of the abs. configuration of the benzylic alc. The transformation of the chiral dihydrooxazines into other selectively protected aminodiols is also documented. [on SciFinder (R)]Crystal structure; Molecular structure (of allyloxyphenyl heterocyclic derivs.); Hydrolysis (prepn. and hydrolysis of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); Stereoselective synthesis (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); Heterocyclic compounds Role: PRP (Properties)RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); Glycols Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); Cyclization (regioselective; prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); Cyclization (stereoselective; prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates)asym synthesis dihydrooxazine deriv cyclization bistrichloroacetimidate intermediate; mol crystal structure dihydro oxazine deriv; diaminoalc prepntext::journal::journal article::research article