InBr 3-catalyzed cyclization of glycosides with arylamines

Pingyuan Wang, Meining Wang, Xuefeng Zhang, Guangfu Yang, Ao Zhang

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr 3 or InI 3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)5386-5390
Number of pages5
JournalTetrahedron
Volume68
Issue number27-28
DOIs
StatePublished - Jul 8 2012
Externally publishedYes

Fingerprint

Cyclization
Glycosides
Moisture
Alcohols
Catalysts
Substrates
alkoxyl radical

Keywords

  • Diastereoselectivity
  • Glycal
  • Glycosidation
  • Glycoside
  • InBr

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Wang, P., Wang, M., Zhang, X., Yang, G., & Zhang, A. (2012). InBr 3-catalyzed cyclization of glycosides with arylamines. Tetrahedron, 68(27-28), 5386-5390. https://doi.org/10.1016/j.tet.2012.04.116

InBr 3-catalyzed cyclization of glycosides with arylamines. / Wang, Pingyuan; Wang, Meining; Zhang, Xuefeng; Yang, Guangfu; Zhang, Ao.

In: Tetrahedron, Vol. 68, No. 27-28, 08.07.2012, p. 5386-5390.

Research output: Contribution to journalArticle

Wang, P, Wang, M, Zhang, X, Yang, G & Zhang, A 2012, 'InBr 3-catalyzed cyclization of glycosides with arylamines', Tetrahedron, vol. 68, no. 27-28, pp. 5386-5390. https://doi.org/10.1016/j.tet.2012.04.116
Wang, Pingyuan ; Wang, Meining ; Zhang, Xuefeng ; Yang, Guangfu ; Zhang, Ao. / InBr 3-catalyzed cyclization of glycosides with arylamines. In: Tetrahedron. 2012 ; Vol. 68, No. 27-28. pp. 5386-5390.
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