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

Tony Kung Ming Shing, Yong Li Zhong

Research output: Contribution to journalArticle

16 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 languageEnglish
Pages (from-to)1573-1579
Number of pages7
JournalTetrahedron
Volume57
Issue number8
DOIs
Publication statusPublished - 2001 Feb 18
Externally publishedYes

Fingerprint

Cycloaddition
Monosaccharides
Cycloaddition Reaction
Alkenes
Mannose
Glucose
nitrones
allose
D-altrose

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition. / Shing, Tony Kung Ming; Zhong, Yong Li.

In: Tetrahedron, Vol. 57, No. 8, 18.02.2001, p. 1573-1579.

Research output: Contribution to journalArticle

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