Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction

Chandra S. Azad, Pratibha Shukla, Mark A. Olson*, Anudeep K. Narula

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach. This new and quite mild catalytic system, comprised of phenylphosphinic acid/NaI, was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.

Original languageEnglish (US)
Pages (from-to)1503-1510
Number of pages8
JournalChinese Journal of Chemistry
Volume39
Issue number6
DOIs
StatePublished - Jun 2021

Keywords

  • Azasugars
  • Isocyanide
  • Multicomponent reactions
  • Nitrilium ion
  • Reductivecyclization

ASJC Scopus subject areas

  • Chemistry(all)

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