Journal ArticleDOI
Intramolecular cycloaddition of 3-O-cyclohexenyl carbohydrate nitrones: Diastereoselective synthesis of optically pure tetrahydropyrano[2,3]cyclohexane derivatives
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TLDR
The intramolecular cycloaddition of nitrones derived from 3- O -cyclohexenylfuranoside-5-aldehydes led to diastereoselective formation of tetrahydropyrano[2,3] cyclohexane ring systems with six chiral centres.About:
This article is published in Tetrahedron Letters.The article was published on 1996-10-14. It has received 4 citations till now. The article focuses on the topics: Cycloaddition & Ring (chemistry).read more
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Journal ArticleDOI
1,3-Dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes
TL;DR: In this paper, a review aims to summarise key features of the synthesis and 1,3-dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes, allowing access to oxazolines and isoxazolidines.
Journal ArticleDOI
Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)
Ashoke Bhattacharjee,Seema Datta,Partha Chattopadhyay,Nanda Ghoshal,Asish P. Kundu,Arani Pal,Ranjan Mukhopadhyay,Sandip Chowdhury,Anup Bhattacharjya,Amarendra Patra +9 more
TL;DR: In this article, the regioselectivity of 3-OACNC was found to depend on the structural nature of the nitrone substitution and stereochemistry at 3-C of the carbohydrate backbone.
Journal ArticleDOI
Cyclization in situ of enose-/ynose-nitrilimines: an expedient approach to the synthesis of chiral glycopyrazoles and pyrazolonucleosides
TL;DR: Intramolecular nitrilimine cycloaddition reactions on carbohydrate-derived substrates proceed in a regioselective fashion, affording structurally novel chiral glycopyrazoles in good yields.
Journal ArticleDOI
Intramolecular Cycloaddition of 3-O-Cyclohexenyl Carbohydrate Nitrones: Diastereoselective Synthesis of Optically Pure Tetrahydropyrano(2,3) cyclohexane Derivatives.
TL;DR: The intramolecular cycloaddition of nitrones derived from 3- O -cyclohexenylfuranoside-5-aldehydes led to diastereoselective formation of tetrahydropyrano[2,3] cyclohexane ring systems with six chiral centres as discussed by the authors.
References
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Journal ArticleDOI
Synthesis of optically pure tetrahydrofurans from 2-o-allylglucose derivatives by intramolecular nitrone cycloaddition: preferential formation of a furanoisoxazolidine from penta-o-allylglucose
TL;DR: In this paper, an intramolecular nitrone cycloaddition of 2-O -allyl-3,5,6-tri-tri O -benzylglucose and penta-O-allylglucoses afforded optically pure trisubstituted tetrahydrofurans.
Journal ArticleDOI
Synthesis of enantiomeric pyrans from a 3-O-allylallose derivative by the application of intramolecular nitrone cycloaddition
TL;DR: The intramolecular nitrone cycloaddition of three sets of 3-O -allylpyranose and the corresponding homochiral 3- O -allylfuranose-5-aldehyde derivatives was studied in this article, which gave rise to only pyran derivatives which were converted to enantiomeric pyranoisoxazolidines via minor degradations.
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Ring‐Selective Synthesis of O‐Heterocycles from Acyclic 3‐O‐Allyl‐monosaccharides via Intramolecular Nitrone—Alkene Cycloaddition.
Tony K. M. Shing,Yong-Li Zhong +1 more