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Volumn , Issue 15, 2008, Pages 2345-2347

[1,2]-Wittig rearrangement of (benzyloxy)acetamides

Author keywords

1,2 Wittig rearrangement; Amides; Phase transfer catalysis

Indexed keywords

(BENZYLOXY)ACETAMIDE DERIVATIVE; ACETAMIDE DERIVATIVE; ALPHA HYDROXYAMIDE DERIVATIVE; AMIDE; UNCLASSIFIED DRUG;

EID: 52949101355     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078268     Document Type: Article
Times cited : (8)

References (36)
  • 2
    • 0000535071 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: London
    • (a) Marshall, J. A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991, 975.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 975
    • Marshall, J.A.1
  • 8
    • 0001501146 scopus 로고    scopus 로고
    • Synthetic applications of [1,2]-Wittig rearrangement: (a) Schreiber, S. L.; Goulet, M. T.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 4718.
    • Synthetic applications of [1,2]-Wittig rearrangement: (a) Schreiber, S. L.; Goulet, M. T.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 4718.
  • 24
    • 52949151092 scopus 로고    scopus 로고
    • 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
    • 2, 0°C (60% over 3 steps).
  • 25
    • 52949142150 scopus 로고    scopus 로고
    • 2 (PE-EtOAc) to afford α-hydroxyamide 4.
    • 2 (PE-EtOAc) to afford α-hydroxyamide 4.
  • 35
    • 52949114445 scopus 로고    scopus 로고
    • minor in all cases.
    • minor in all cases.
  • 36
    • 52949112188 scopus 로고    scopus 로고
    • 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
    • minor = 5.0 Hz. Therefore, the syn stereochemistry remained ambiguous in this latter case.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.