Diastereoselective 1,3-dipolar intramolecular nitrone olefin cycloaddition (INOC) reaction of a sugar-derived allyl alcohol: Synthesis of functionalized aminocyclopentitols

The DIBAL-H reduction of the Baylis-Hillman sugar adduct, obtained from 3-O-benzyl-1,2-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose yielded trisubstituted alkenes by eliminating the β-hydroxyl group. Subsequently, the hydrolysis of the isopropylidene acetal to the corresponding hemiacetal was re...

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Bibliographic Details
Published in:Carbohydrate research 2024-09, Vol.543, p.109223, Article 109223
Main Author: Rohokale, Rajendra
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Aminocyclopentitol
Baylis–hillman reaction
Carbohydrate
Cycloaddition Reaction
Diastereoselectivity
Molecular Structure
Nitrogen Oxides - chemistry
Nitrone cycloaddition
Propanols - chemistry
Stereoisomerism
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Summary:The DIBAL-H reduction of the Baylis-Hillman sugar adduct, obtained from 3-O-benzyl-1,2-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose yielded trisubstituted alkenes by eliminating the β-hydroxyl group. Subsequently, the hydrolysis of the isopropylidene acetal to the corresponding hemiacetal was reacted with N-benzyl hydroxylamine hydrochloride to generate the nitrone, which underwent diastereoselective intramolecular 1,3-dipolar nitrone olefin cycloaddition (INOC) to give an isoxazolidine skeleton. The concomitant reductive cleavage of the N-O bond and benzyl group of the fused isoxazolidines afforded new functionalized aminocyclopentitols in good yields. [Display omitted]
ISSN:0008-6215
1873-426X
1873-426X
DOI:10.1016/j.carres.2024.109223