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ChemInform Abstract: Stereoselectivity in the Birch Reduction of 2-Furoic Acid Derivatives.

✍ Scribed by T. J. DONOHOE; M. HELLIWELL; C. A. STEVENSON; T. LADDUWAHETTY

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselectivity in the Birch Reduction of 2-Furoic Acid Derivatives.

-Birch reduction of the chiral amide (I) of 2-furoic acid and following electrophilic quench gives the dihydrofuroic amides (III) with high diastereoselectivity. Acidic cleavage of the chiral auxiliary liberates the carboxylic acids (IV) of high enantiopurity. Surprisingly, the amide (V) derived from mild acidic quench of the Birch reduction is resistant to hydrolysis. -(DONOHOE, T.

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