MacMillan Imidazolidinone Organocatalysts [Asymmetric Synthesis]

The imidazolidinone derivatives (Product No. B4137 and B4138) are asymmetric organocatalysts developed by MacMillan et al. To date, various types of asymmetric reactions using the imidazolidinone derivatives have been reported, such as Mukaiyama-Michael addition,¹⁾ epoxidation of α,β-unsaturated aldehydes,²⁾ 1,3-addition of aldehydes,³⁾ and the Diels-Alder reaction.⁴⁾ The desired products are realized in high yields and selectivity in all the cases.

References

• 1) The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction:  A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architectures
  • S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192.
• 2) Enantioselective organocatalytic epoxidation using hypervalent iodine reagents
  • S. Lee, D. W. C. MacMillan, Tetrahedron 2006, 62, 11413.
• 3) Enantioselective Organocatalytic Singly Occupied Molecular Orbital Activation:  The Enantioselective α-Enolation of Aldehydes
  • H.-Y. Jang, J.-B. Hong, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 7004.
• 4) Enantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D
  • R. M. Wilson, W. S. Jen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 11616.