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 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 car...
| Hlavní autoři: | , , , |
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| Médium: | Journal article |
| Jazyk: | English |
| Vydáno: |
1998
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| Shrnutí: | 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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