The regiochemistry of reduction of mono-ethyl fumarate and maleate using a ruthenium BINAP catalyst

Add time:07/25/2019    Source:sciencedirect.com

The regiochemistry of the reduction of mono-ethyl fumarate using bis(carboxylato){2,2′-bis(diphenylphosphino)-[R]-1,1-binapthyl}-ruthenium(II) (Ru[BINAP]) in H2/CH3OD is reported and occurs opposite to the regiochemistry observed in the reduction of tiglic acid. Reduction of mono-ethyl maleate with D2/CH3OD is very sluggish but produces meso-dideuteriosuccinic acid with high stereoselectivity. Reduction of mono-ethyl maleate with Ru[BINAP](O2CR)2 and H2/CH3OD results in mono-ethyl succinate-d1 with nearly complete loss of regiochemistry.

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