Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates

An 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)]


Published in:
Organic Letters, 9, 2, 247-250
Year:
2007
Keywords:
Note:
CAN 146:251764
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
925703-62-4P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (crystal structure; prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); 925703-68-0P; 925703-74-8P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (crystal structure; prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); 84-85-5 (4-Methoxy-1-Naphthalenol); 90-15-3 (1-Naphthalenol); 98-54-4; 106-95-6 (Allyl bromide); 135-19-3 (2-Naphthalenol); 150-19-6; 533-31-3 (1,3-Benzodioxol-5-ol); 545-06-2 (Trichloroacetonitrile); 2033-89-8; 50827-64-0; 102308-32-7 (Garner's aldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); 116079-35-7P; 925703-60-2P; 925703-63-5P; 925703-64-6P; 925703-66-8P; 925703-70-4P; 925703-84-0P; 925703-87-3P; 925703-89-5P; 925703-93-1P; 925703-95-3P; 925703-97-5P; 925703-99-7P; 925704-01-4P; 925704-02-5P; 925704-04-7P; 925704-06-9P; 925704-08-1P; 925704-10-5P; 925704-12-7P; 925704-30-9P; 925704-32-1P; 925704-34-3P; 925704-36-5P; 925704-38-7P; 925704-40-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates); 925703-72-6P; 925704-14-9P; 925704-16-1P; 925704-18-3P; 925704-20-7P; 925704-22-9P; 925704-24-1P; 925704-26-3P; 925704-28-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of chiral dihydrooazines from arylaminopropane diols via bistrichloroacetimidate intermediates)
Laboratories:




 Record created 2010-11-25, last modified 2018-12-03


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