Palladium-Catalyzed Reduction of Allylic Esters

By: William Sommer, Aldrich ChemFiles 2008, 8.6, 4.

The palladium catalyzed reduction of allylic esters provides a convenient method to access chiral olefins.1Hayashi et al. studied the activity of the MOP ligand with palladium toward the reduction of allylic esters.2 Mechanistic studies of the reaction have showed that a monodentate phosphine ligand is essential to achieve high selectivity. Reacting geranyl methyl carbonate with Pd2(dba)3 and MOP (1 mol% respectively), quantitatively yielded (S)-3,7-dimethyl-1,6-octadiene with 76%ee (Scheme 2). It is important to note that a low catalyst and ligand loading with mild conditions is necessary for good selectivity.


Scheme 2.

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Materials

     

Aldrich ChemFiles 2008, 8.6, 4.

References

  1. Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
  2. Hayashi, T. et al. J. Am. Chem. Soc. 1994, 116, 775. Hayashi, T. et al. Synthesis 1994, 526.

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