Tetrahedron Letters p. 3071 - 3074 (1998)
Update date:2022-08-16
Topics:
Donohoe, Timothy J.
Helliwell, Madeleine
Stevenson, Clare A.
Ladduwahetty, Tamara
The preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a Ca 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.
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