An efficient, palladium-catalyzed, enantioselective synthesis of (2R)-3-butene-1,2-diol and its use in highly selective Heck reactions

1. 

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   Fig. 1.

   Dynamic kinetic asymmetric transformations of 3,4-epoxy-1-butene. Pd₂dba₃·CHCl₃, tris(dibenzylideneacetone)dipalladium(0)·chloroform adduct.

   
   
2. 

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   Fig. 2.

   Initial studies to produce 1 via the cyclic carbonate 7.

   
   
3. 

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   Fig. 3.

   Optimized route to diol 1.

   
   
4. 

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   Fig. 4.

   Reaction pathways for Heck reactions of 8 and 9.