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 manno...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011-11, Vol.2011 (32), p.6405-6408
Main Authors: Cao, Hai Thuong, Roisnel, Thierry, Grée, René
Format: Article
Language:English
Subjects:
Alcohols
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Aminocyclopentitols
Chemical Sciences
Chemistry
Domino reactions
Exact sciences and technology
Iron
Mannich reaction
Organic chemistry
Preparations and properties
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Summary: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. New aminocyclitols are easily obtained through a short sequence including an iron‐catalyzed tandem isomerization–Mannich reaction as a key step. By using N‐tert‐butanesulfinamides, this methodology allowed efficient enantioselective synthesis of a mannostatine A analogue and two stereoisomers of known fucosidase and glycosidase inhibitors.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101130