4.5 Article

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

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 6, Pages 1503-1510

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000634

Keywords

Azasugars; Multicomponent reactions; Nitrilium ion; Isocyanide; Reductivecyclization

Funding

  1. Tianjin University
  2. GGS IP Universality

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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, with high yields achieved for both L-allo-DNJ and L-altro-DNJ.
Main observation and conclusion 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.

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