Skip to Content
Merck
  • InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.

InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.

The Journal of organic chemistry (2011-03-11)
Fulong Li, Chunyong Ding, Meining Wang, Qizheng Yao, Ao Zhang
ABSTRACT

To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr(3) as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyclopentanone, ReagentPlus®, ≥99%
Supelco
Cyclopentanone, analytical standard
Sigma-Aldrich
Cyclopentanone, ≥99%, FG