Applications of Carbohydrate-Based Organocatalysts in Enantioselective Synthesis

• Published in: European journal of organic chemistry Vol. 2014; no. 33; pp. 7291 - 7303
• Main Author: Faisca Phillips, Ana Maria
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.11.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Asymmetric synthesis; Bifunctional catalysts; Carbohydrates; Organocatalysis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201402689

Carbohydrates have been widely used for stereochemical control, either as chiral auxiliaries or as ligands. Their natural abundance and rigidity of structure, together with the presence of many functional groups, have also in recent years made them attractive chiral modular units for the assembly of bifunctional organocatalysts. Applications have ranged from the more complex bifunctional carbohydrate‐based amine–(thio)ureas and prolinamides to simple amino alcohols. The presence of many hydroxy groups and their consequent water solubility has allowed for the study of reactions in aqueous media. Nowadays they have been applied to many reactions such as the aldol, Michael, Stetter, Biginelli, Morita–Baylis–Hillman, decarboxylative Mannich and other reactions, and even to the multistep synthesis of known drugs. This review provides an overview of developments in this field in the period from 2009 to mid‐2014. Carbohydrates, with their rigid backbones, large numbers of functional groups and high contents of chiral centres, are an appealing natural resource for the development of organocatalysts. They are becoming increasingly popular new tools for enantioselective synthesis, and this subject is reviewed for the period from 2009 to mid‐2014.