Stereoselectivity in the Birch reduction of 2-furoic acid derivatives

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 ca...

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Bibliographic Details
Published in:Tetrahedron letters 1998-05, Vol.39 (19), p.3071-3074
Main Authors: Donohoe, Timothy J, Helliwell, Madeleine, Stevenson, Clare A, Ladduwahetty, Tamara
Format: Article
Language:English
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00361-X