Stereoselective syntheses of the methylene- and α-fluoromethylene-phosphonate analogues of 2-phospho-D-glyceric acid
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 4,p. 317-319
- https://doi.org/10.1039/c39880000317
Abstract
An enantioselective synthesis is described for the preparation of (2R)-2-carboxy-3-hydroxypropane-1-phosphonic acid (1), an isosteric analogue of 2-phospho-D-glyceric acid (2), from L-threose; the route is extended to provide diastereoselective syntheses of both (1R,2R)- and (1S,2R)-2-carboxy-1-fluoro-3-hydroxypropane-1-phosphonic acids (3) and (4) respectively which provide the first examples of the synthesis of α-fluoroalkanephosphonates of defined chirality at C-1.Keywords
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