Proline-Based Organocatalysts [Asymmetric Synthesis]

Pioneering work in this area dates back to the 1970s in which Eder et al. and Hajos et al. separately reported an intramolecular asymmetric aldol reaction which employed L-proline (Product No. P0481) as a catalyst.^1,2) Later in 2000, List et al. reported an L-proline-catalyzed intermolecular asymmetric aldol reaction.³⁾ The same year, MacMillan et al. documented the first highly enantioselective amine-catalyzed Diels-Alder reaction.⁴⁾ TCI offers proline-type organocatalyts like Singh's catalyst (Product No. H1407),⁵⁾ Hayashi-Jorgensen catalysts (Product No. D3843 and D3867),^6,7) etc.

References

• 1) New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures
  • U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. 1971, 10, 496.
• 2) Asymmetric synthesis of bicyclic intermediates of natural product chemistry
  • Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615.
• 3) Proline-Catalyzed Direct Asymmetric Aldol Reactions
  • B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.
• 4) New Strategies for Organic Catalysis:  The First Highly Enantioselective Organocatalytic Diels−Alder Reaction
  • K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243.
• 5) Highly Enantioselective Direct Aldol Reaction Catalyzed by Organic Molecules
  • M. Raj, V. Maya, S. K. Ginotra, V. K. Singh, Org. Lett. 2006, 8, 4097.
• 6) Enantioselective Organocatalyzed α Sulfenylation of Aldehydes
  • M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. Int. Ed. 2005, 44, 794.
• 7) Diphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
  • Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212.