Intramolecular Tandem Isomerization–Mannich Reaction as a New Route Towards Aminocyclopentitols
A new efficient synthetic strategy has been developed to prepare aminocyclopentitols. It is based on an iron-catalyzed tandem isomerization-Mannich reaction and uses chiral N-tert-butanesulfinamide as a chiral auxiliary. This methodology has been applied to the enantiocontrolled synthesis of a mannostatin A analogue, as well as isomers of known fucosidase and glycosidase inhibitors.