Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition

Tony K.M. Shing; Yong Li Zhong

doi:10.1016/S0040-4020(00)01138-8

Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition

Tony K.M. Shing, Yong Li Zhong

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-D-glucose and D-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-D-allose and D-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively.

Original language	English
Pages (from-to)	1573-1579
Number of pages	7
Journal	Tetrahedron
Volume	57
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(00)01138-8
Publication status	Published - 2001 Feb 18
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition",

abstract = "Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-D-glucose and D-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-D-allose and D-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively.",

author = "Shing, {Tony K.M.} and Zhong, {Yong Li}",

note = "Funding Information: This research was supported by the Hong Kong RGC Earmarked Grant (Ref. No. CUHK457/95P).",

year = "2001",

month = feb,

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doi = "10.1016/S0040-4020(00)01138-8",

language = "English",

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pages = "1573--1579",

journal = "Tetrahedron",

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T1 - Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition

AU - Shing, Tony K.M.

AU - Zhong, Yong Li

N1 - Funding Information: This research was supported by the Hong Kong RGC Earmarked Grant (Ref. No. CUHK457/95P).

PY - 2001/2/18

Y1 - 2001/2/18

N2 - Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-D-glucose and D-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-D-allose and D-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively.

AB - Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-D-glucose and D-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-D-allose and D-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively.

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UR - http://www.scopus.com/inward/citedby.url?scp=0035906031&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(00)01138-8

DO - 10.1016/S0040-4020(00)01138-8

M3 - Article

AN - SCOPUS:0035906031

SN - 0040-4020

VL - 57

SP - 1573

EP - 1579

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition

Abstract

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