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Volumn , Issue 5, 2008, Pages 663-666

Novel catalytic synthetic route to protected α-methyl threonine and the first asymmetric acetyl migration in a steglich rearrangement reaction

(2) Dietz, Friedrich R a Gröger, Harald a

a UNIVERSITY OF ERLANGEN NUREMBERG (Germany)

Author keywords

Acylation; Amino acids; Asymmetric catalysis; Rearrangements; Stereoselective synthesis

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; ALPHA METHYL THREONINE; SODIUM BOROHYDRIDE; THREONINE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOSELECTIVITY; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

EID: 41349086248 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032104 Document Type: Article

Times cited : (37)

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28
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- Preparation of rac-2-Benzoylamino-2-methyl-3- oxobutyric Acid Isopropyl Ester (rac-6) 4-Acetyl-4-methyl-2- phenyloxazol-5-one (rac-7, 1.5 g, 6.9 mmol) and DMAP (10, 90 mg, 0.7 mmol) were dissolved in i-PrOH (40 mL, The reaction mixture was stirred for 16 h and the excess of i-PrOH was removed in vacuo. The resulting crude product was purified by column chromatography [SiO2 60 Å, cyclohexane-EtOAc (3:1, to give rac-6 (1.62 g, 5.8 mmol, 84% yield, 1H NMR (400 MHz, CDCl3, δ, 1.18 (3 H, d, J, 6.3 Hz, 1.21 (3 H, d, J, 6.3 Hz, 1.79 (3 H, s, 2.21 (3 H, s, 5.08 (1 H, sept, J, 6.3 Hz, 7.40-7.44 (2 H, m, 7.48-7.52 (1 H, m, 7.71 (1 H, br s, 7.78-7.81 (2 H, m) ppm. 13C NMR (100 MHz, CDCl3, δ, 19.97, 21.36, 21.39, 23.97, 68.62, 70.51, 127.02, 128.58, 131.84, 133.51, 165.85, 168.56, 200.23 ppm. MS EI
- 4: C, 64.97; H, 6.91; N, 5.05. Found: C, 64.61; H, 6.88; N, 4.89.

29
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- Preparation of Diastereomers of rac-2-Benzoylamino-3- hydroxy-2-methylbutyric Acid Isopropyl Ester (rac-l-5, rac-u-5) 2-Benzoylamino-2-methyl-3-oxobutyric acid isopropyl ester (rac-6, 200 mg, 0.72 mmol) was dissolved in i-PrOH (20 mL) and cooled in an ice bath. After adding NaBH4 (13.6 mg, 0.36 mmol) the mixture was stirred at ice-bath temperature for 2 h, and further 2 h at r.t. Subsequently, dilute HCl was added until no further hydrogen was evolved. After addition of H2O the reaction mixture was extracted 5 times with MTBE. Removal of the solvent furnished a crude product of the resulting racemic diastereomers l-5 and u-5 (dr, 60:40, which were separated by column chromatography [SiO2 60 Å, cyclohexane-EtOAc (3:1, to give rac-l-5 (36 mg, 0.13 mmol, 18, and rac-u-5 37 mg, 0.13 mmol, 18, Compound rac-l
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36
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37
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- Experimental Procedure (Exemplified for Reaction in Table 1, Entry 1) 5-Acetyloxy-4-methyl-2-phenyloxazole (8, 500 mg, 2.3 mmol) and 4-dimethylaminopyridinyl-(pentaphenylcyclopentadienyl)iron, S)-11, 40 mg, 0.06 mmol] were dissolved in CH2Cl2 (20 mL) and stirred at r.t. for 3 h. Subsequently the solvent was removed to give 4-acetyl-4-methyl-2-phenyloxazol-5-one 7 (537 mg) as an oily crude product. The conversion (84, and enantioselectivity (25% ee) were determined by 1H NMR spectroscopy and chiral HPLC chromatography [after derivatization to 6, Daicel Chiralcel OD column, hexane/2-PrOH (97:3, respectively. The spectroscopic properties are in accordance with those for the racemic product rac-7. The other reactions with catalyst (S)-11 (Table 1, entries 2-4) as well as the reaction with, )-tetramisole, S)-12] as a catalyst in CH2Cl 2 Table 1, e
- 1H NMR spectroscopy in this experiment.

38
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39
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- The Birman group also reported that benzotetramisole turned out to be an improved and very efficient organocatalyst in resolution processes compared with, )-tetramisole, S-12, Thus, this catalyst might also give improved enantioselectivities in the synthesis of 7, which is planned to be studied next
- (b) The Birman group also reported that benzotetramisole turned out to be an improved and very efficient organocatalyst in resolution processes compared with (-)-tetramisole [(S)-12]. Thus, this catalyst might also give improved enantioselectivities in the synthesis of 7, which is planned to be studied next.

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