| Abstrakt: |
The history of proline sulfonamides for use in catalyzing highly enantioselective and diastereoselective C-C bond forming reactions is described. Highlighted is the development of N-( P-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide ('Hua Cat') and N-(carboxy- P-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide ('Hua Cat-II') by Yang and Carter. Specific reactions covered include the aldol reaction, Mannich reaction, formal aza-Diels-Alder reaction, tandem Michael/Mannich reaction and Yamada-Otani ?reaction. The ability of proline aryl sulfonamides to construct all-carbon quaternary stereocenters in high enantioselectivity and dia?stereoselectivity is a notable feature of the reported work. The practicality of this chemistry for large scale and industrial applications is also included. Finally, a discussion of the future directions of proline sulfonamide organocatalysis is provided. 1 Introduction 2 Proline Sulfonamides 2.1 Synthesis of First Proline Sulfonamides 2.2 Early Proline Sulfonamide Organocatalysis 3 Hua Cat 3.1 Discovery of Hua Cat 3.2 Intramolecular Michael Additions 3.3 Aldol Reactions 3.4 Mannich Reactions 3.5 Aza-Diels-Alder Reactions 3.6 Quaternary Center Formation 3.7 Stereogenic, All-Carbon Quaternary Center Formation in Bicyclic Scaffolds 3.8 Yamada-Otani Reaction and Hua Cat-II 4 Future Directions 5 Conclusion [ABSTRACT FROM AUTHOR] |
