Diastereoselective Cyclopropanation

The treatment of unsaturated amines with electrophiles presents issues with chemoselectivity as the nitrogen lone pair and the olefinic bond are both potential sites for reaction. We have developed a range of methodologies to combat this problem and developed several stereoselective processes, such as the chemo- and diastereoselective cyclopropanation protocols described below, that have proven useful in total synthesis.

We have also developed a chemo- and stereoselective cyclopropanation reaction of allylic amines, and a stereodivergent, diastereoselective cyclopropanation protocol of allylic carbamates using the Wittig-Furukawa reagent [Zn(CH2I)2] or Shi’s carbenoid [CF3CO2ZnCH2I].
 

Diastereoselective cyclopropanation
 

Key Publications: 

  1. Chemo- and diastereoselective cyclopropanation of allylic amines and carbamates
    Csatayová, K.; Davies, S. G.; Lee, J. A.; Ling, K. B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Tetrahedron 2010, 66, 8420 [View Journal Page]
  2. Syntheses of trans-SCH-A and cis-SCH-A via a stereodivergent cyclopropanation protocol
    Csatayová, K.; Davies, S. G.; Lee, J. A.; Ling, K. B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Org. Lett. 2010, 12, 3152 [View Journal Page]
  3. Diastereoselective Simmons-Smith cyclopropanations of allylic amines and carbamates
    Davies, S. G.; Ling, K. B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Chem. Commun. 2007, 4029
    [View Journal Page]

 

 

 

 

 


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