Stereospecific synthesis of α-deuteriated α-amino acids: regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 157-165
- https://doi.org/10.1039/p19950000157
Abstract
Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines in refluxing CH3O2H–2H2O gives the [6-2H2]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-α-deuteriated α-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.Keywords
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