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Stereoselectivity in the birch reduction of 2-furoic acid derivatives

Abstract:
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.
Publication status:
Published

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
39
Issue:
19
Pages:
3071-3074
Publication date:
1998-05-07
DOI:
ISSN:
0040-4039
Source identifiers:
36484
Language:
English
Pubs id:
pubs:36484
UUID:
uuid:a7f7bbed-d40f-4fef-a091-bfecb914f2ea
Local pid:
pubs:36484
Deposit date:
2012-12-19

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