research article

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

Rondot, Christophe
•
Retailleau, Pascal
•
Zhu, Jieping  
2007
Organic Letters

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)]

Type
research article
DOI
10.1021/ol0627202
Author(s)
Rondot, Christophe
Retailleau, Pascal
Zhu, Jieping  
Date Issued

2007

Published in
Organic Letters
Volume

9

Issue

2

Start page

247

End page

250

Subjects

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 prepn

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

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58428