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Volumn 46, Issue 16, 2005, Pages 2751-2755

Direct synthesis of N-substituted, functionalized aspartic acids using alkali maleates and amines

Author keywords

Aspartic acid derivatives; Chemoselectivity; Conjugate addition; Lithium, sodium

Indexed keywords

ALKALI; AMINE; ASPARTIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; MALEIC ACID DERIVATIVE;

EID: 15944389493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.159     Document Type: Article
Times cited : (13)

References (43)
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    • For recent reviews on the synthesis of β-amino acids, see: M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991 8035
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    • 85030806035 scopus 로고    scopus 로고
    • Japanese Patent, 2000, 2000.136.172
    • Additions of long, straight-chain alkylamines have been reported in the patent literature. For an example, see: Yamamoto, A.; Kobayashi, Y.; Mori, Y. Japanese Patent, 2000, 2000.136.172
    • Yamamoto, A.1    Kobayashi, Y.2    Mori, Y.3
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    • note
    • Similar observations have been made earlier by Liwschitz and Irsay (quoted by Zilcha and Bachi, see Footnote 5 in Ref. 16). They note that "... reaction of other amines with maleic acid either in aqueous solution or otherwise did not give the required N-alkyl-aspartic acid but led to the formation of amine salts of maleic acid or to unidentified products"
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    • note
    • The solvents screened included DMF, tetrabutylurea, tetramethylurea, tri-n-butylphosphate, N-methylpyrrolidone and 1,3-dimethyl-3,4,5,6-tetrahydro- 2(1H)-pyrimidinone (DMPU)
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    • note
    • Isomerization of a 0.1 M solution of maleic acid into fumaric acid was attempted at 125°C in DMSO for 72 h. Less than 1% isomerization could be detected during this period. A control experiment with added NaBr (200 mol %) gave identical results. A mixture of maleic acid (3 mmol), n-hexylamine (1 mmol) and NaBr (6 mmol) in DMSO did not give any reaction even at +125°C except for the slow formation of n-hexylmaleamide
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    • Chem. Abstr. 90 1978 168021
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