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Synlett 2010(19): 2827-2838  
DOI: 10.1055/s-0030-1259020
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Proline Sulfonamide Based Organocatalysis: Better Late than Never

Hua Yang, Rich G. Carter*
Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA
Fax: +1(541)7379486; e-Mail: rich.carter@oregonstate.edu;
Further Information

Publication History

Received 7 September 2010
Publication Date:
03 November 2010 (online)

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Abstract

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 dia­stereoselectivity 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

Key words

asymmetric catalysis - amino acids - enantioselectivity - sulfonamides - solvent effects - aldol reaction - multicomponent reaction - Michael addition - phase-transfer catalysis