Stereoselectivity in the Birch reduction of 2-furoic acid derivatives

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Stereoselectivity in the Birch reduction of 2-furoic acid derivatives

Donohoe, Timothy J; Helliwell, Madeleine; Stevenson, Clare A; Ladduwahetty, Tamara

Tetrahedron letters, 05/1998, Volume: 39, Issue: 19

Journal Article

The preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a C 2 symmetrical amine as a chiral auxiliary, very high levels of sterochemical control could be obtained. Moreover, the auxiliary could be removed conveniently by heating in 6M HCl to liberate a carboxylic acid of high enantiomeric purity. The relative stereochemistry of the Birch reduced amides (and therefore the absolute stereochemistry of the corresponding acids) was determined unambiguously from an X-ray crystal structure. The stereoselective Birch reduction of 3-methyl-2-furoic acid derivatives is described.

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Donohoe, Timothy J | Helliwell, Madeleine | Stevenson, Clare A | Ladduwahetty, Tamara

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