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52949151092
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Representative Procedure for the Preparation of (Benzyloxy)acetamides 3 To a solution of alcohol 1 (1.1 mmol) and bromoacetylpyrrolidine (2, 1 mmol) in toluene (15 mL, at r.t, was added n-Bu 4NHSO4 (0.2 mmol) and a 35% aq NaOH solution (15 mL, The mixture was then stirred vigorously at r.t, and the reaction was monitored by TLC. After 3-4 h, H2O (20 mL) and Et2O (20 mL) were added at 0°C. The aqueous layer was extracted with Et2O (5 x 30 mL, and the combined organic layers were washed with sat. aq NH4Cl soln (50 mL, dried over MgSO4, and concentrated in vacuo. The crude residue was purified on SiO2 (PE-EtOAc) to afford(benzyloxy)acetamide 3. Amide 3k with R1, CH2)2OTBS (Table 2, entry 11) was obtained from amide 3f (Table 1, entry 6) by using the following sequence: 1) O3, MeOH, 78°C then Ph
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2, 0°C (60% over 3 steps).
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25
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52949142150
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2 (PE-EtOAc) to afford α-hydroxyamide 4.
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2 (PE-EtOAc) to afford α-hydroxyamide 4.
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0030567340
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Tomooka, K.; Yamamoto, H.; Nakai, T. J. Am. Chem. Soc. 1996, 118, 3317.
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Slobedman, D.4
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52949114445
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minor in all cases.
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minor in all cases.
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36
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52949112188
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In all cases 3Jmajor > 3Jminor except for hydroxyamide 4i Table 2, entry 9, For compound 4i, 3Jmajor, 4.3 Hz and 3Jminor, 5.0 Hz. Therefore, the syn stereochemistry remained ambiguous in this latter case
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minor = 5.0 Hz. Therefore, the syn stereochemistry remained ambiguous in this latter case.
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