Synthesis of enantiomerically pure α-amino acids via chemo- and diastereoselective alkylation of (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

Tetrahedron Asymmetry

Volumn 8, Issue 24, 1997, Pages 4007-4010

  Harwood, Laurence M ^a   Tyler, Simon N G ^a   Anslow, A Susan ^b   MacGilp, Iain D ^b   Drew, Michael G B ^a  

^a UNIVERSITY OF READING   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; CRYSTALLOGRAPHY; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584582     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00587-9     Document Type: Article

References (32)

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21. 4 and evaporated in vacua. Purification of the residue by flash column chromatography, eluting with diethyl ether:light petroleum (2:5), followed by recrystallisation from diethyl ether-light petroleum furnished adducts 3 as colourless crystalline solids.
22. 16
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25. General procedure for synthesis of α-amino acids 4: the requisite oxazin-2-one 3 (100 mg, 0.37 mmol) was dissolved in methanol (5 mL) in a Fischer-Porter bottle containing Pearlman's catalyst (100 mg), trifluoroacetic acid (0.1 mL) and water (0.5 mL). The bottle was pressurised with hydrogen to 5 bar and the mixture stirred rapidly for 24 h. After depressurisation the mixture was filtered through Celite® and the solvent evaporated in vacua. The residue was purified by ion-exchange chromatography (Dowex® 50WX8-100) and triturated with diethyl ether to furnish α-amino acids 4 as colourless powders.
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