Synthesis of l-4,4-Difluoroglutamic Acid via Nucleophilic Addition to a Chiral Aldehyde
Fluorine-containing derivatives of amino acids are assuming increasing importance as probes of biological function and enzyme mechanism. We now report a new, flexible route to enantiomerically pure l-4,4-difluoroglutamic acid that exploits the addition of difluorinated nucleophiles to configurationa...
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| Veröffentlicht in: | Journal of organic chemistry 2001-09, Vol.66 (19), p.6381-6388 |
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| container_end_page | 6388 |
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| container_issue | 19 |
| container_start_page | 6381 |
| container_title | Journal of organic chemistry |
| container_volume | 66 |
| creator | Ding, Yun Wang, Jianqiang Abboud, Khalil A Xu, Yuelian Dolbier, William R Richards, Nigel G. J |
| description | Fluorine-containing derivatives of amino acids are assuming increasing importance as probes of biological function and enzyme mechanism. We now report a new, flexible route to enantiomerically pure l-4,4-difluoroglutamic acid that exploits the addition of difluorinated nucleophiles to configurationally stable α-aminoaldehydes. Conversion of the difluorinated adducts to l-4,4-difluoroglutamic acid can be accomplished in three steps by Barton−McCombie dehydroxylation and acid hydrolysis. |
| doi_str_mv | 10.1021/jo015754q |
| format | Article |
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| ispartof | Journal of organic chemistry, 2001-09, Vol.66 (19), p.6381-6388 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Aldehydes - chemistry Aspartate-Ammonia Ligase - chemistry Aspartate-Ammonia Ligase - metabolism Glutamates - chemical synthesis Glutamates - chemistry Glutamates - metabolism Hydrolysis Hydroxylation Molecular Conformation |
| title | Synthesis of l-4,4-Difluoroglutamic Acid via Nucleophilic Addition to a Chiral Aldehyde |
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