Synthesis of different deuterated carboxylic acids from unsaturated acids promoted by samarium diiodide and D2O.
An easy, and rapid reduction of the Cdbond;C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D(2)O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new Cdbond;C bond being generated with complete diastereoselectivity. When H(2)O is used instead of D(2)O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.