A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8453-8456

  Nocioni, Alessandra Maria ^a   Papa, Carmela ^a   Tomasini, Claudia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; IODINE DERIVATIVE; OXAZOLINE DERIVATIVE; PACLITAXEL; PACLITAXEL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033607703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01772-4     Document Type: Article

References (21)

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18. In a typical procedure, NaHMDS (0.44 mmol, sol. 1M in THF, 0.44 mL) was added to a stirred solution of 2a-h (0.2 mmol) in dry THF (5 mL) and the mixture was stirred at room temperature for the scheduled time (see Table 1). Then iodine (0.48 mmol, 0.12 g) in dry THF (10 mL) was added and the mixture was stirred at room temperature for the additional time reported in Table 1. Then an aqueous saturated solution of ammonium chloride was added, THF was eliminated under reduced pressure and replaced with ethyl acetate. The organic layer was washed twice with a saturated solution of sodium thiosulphate, dried over sodium sulphate and concentrated. The residue was chromatographed on silica gel (cyclohexane: ethyl acetate in 8:2 ratio as eluant).
19. Several attempts to detect the presence of the oxazoline were fruitless: these oxazolines cannot be detected by GC-MS, furthermore the TLC analysis of the crude reaction is difficult to understand, owing to the presence of unreacted iodine. When the TLC analysis is performed after work-up with aqueous ammonium chloride and aqueous sodium thiosulphate, only the starting material and the compound 4 are present.
20. 3), 5.50 (d, 1H, J = 9.5 Hz), 7.11 (d, 1H, J = 9.5 Hz, NH), 7.19-7.60 (m, 8H, Ph), 7.65-7.85 (m, 2H, Ph).
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