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

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.

Automated summary

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.