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Volumn 73, Issue 23, 2008, Pages 9334-9339

Convenient synthetic route to an enantiomerically pure FMOC α-amino acid

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; ESTERIFICATION; ESTERS; ORGANIC ACIDS; ORGANIC COMPOUNDS;

EID: 57449108895     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801781v     Document Type: Article
Times cited : (14)

References (63)
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  • 46
    • 0000177311 scopus 로고
    • For our initial paper showing the preparation of α-diazo esters, see: a
    • For our initial paper showing the preparation of α-diazo esters, see: (a) Taber, D. F.; You, K.; Song, Y. J. Org. Chem. 1995, 60, 1093.
    • (1995) J. Org. Chem , vol.60 , pp. 1093
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    • For the initial preparation of α-amino menthyl esters as the hydrochloride salts, see: a
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    • (1964) Bull. Chem. Soc. Jpn , vol.37 , pp. 191
    • Harada, K.1    Hayakawa, T.2
  • 52
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    • For the chromatographic separation of racemic amino acids as their menthyl esters, see: House, D. W. U. S. (1983), 4 pp, CODEN: USXXAM US 4379941 A 19830412.
  • 53
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    • While preparing this manuscript, another example of employing L-menthol as a tool for separating diastereomers was published: Sani, M, Fossati, G, Huguenot, F, Zanda, M. Angew. Chem, Int. Ed. 2007, 46, 3526
    • While preparing this manuscript, another example of employing L-menthol as a tool for separating diastereomers was published: Sani, M.; Fossati, G.; Huguenot, F.; Zanda, M. Angew. Chem., Int. Ed. 2007, 46, 3526.
  • 57
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    • For details of the esterification step, see
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    • For a previous preparation of 5a, see: Sakakura, A.; Kawajiri, K.; Ohkubo, T.; Kosugi, Y.; Ishihara, K. J. Am. Chem. Soc. 2007, 129, 14775.
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    • A slight impurity in the commercial menthol was present at δ 0.56. This impurity did not interfere with the analysis.
    • A slight impurity in the commercial menthol was present at δ 0.56. This impurity did not interfere with the analysis.
  • 63
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    • 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as d and for methylene and quaternary carbons as u.
    • 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as "d" and for methylene and quaternary carbons as "u".


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