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Volumn 49, Issue 18, 2008, Pages 2902-2906

Synthesis of optically enriched 1,2-aminoalcohols by [2,3]-Wittig rearrangements of 3-aza-allylic alcohol derivatives

Author keywords

1,2 Aminoalcohols; 2,3 Wittig rearrangement; Chirality transfer; Diastereoselectivity; Enamides

Indexed keywords

1,2 AMINOALCOHOL DERIVATIVE; 3 AZA ALLYLIC ALCOHOL DERIVATIVE; ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41349103389     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.023     Document Type: Article
Times cited : (20)

References (29)
  • 3
    • 41349118977 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon, London
    • Marshall J.A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, London 908-975
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 908-975
    • Marshall, J.A.1
  • 12
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis. 1st ed. (1999), Springer, Berlin
    • (1999) Comprehensive Asymmetric Catalysis. 1st ed.
  • 15
    • 41349099629 scopus 로고    scopus 로고
    • note
    • H1-H2 = 10.0 Hz) was used to assign the relative configuration. {A figure is presented}
  • 18
    • 0000116376 scopus 로고
    • Alcohol 7 was synthesized according to the sequence depicted in Scheme 3 (5 steps, 79% overall yield) from the corresponding propargylic alcohol (ee ≥ 98%). For the preparation of the latter alcohol, see:
    • Alcohol 7 was synthesized according to the sequence depicted in Scheme 3 (5 steps, 79% overall yield) from the corresponding propargylic alcohol (ee ≥ 98%). For the preparation of the latter alcohol, see:. Yadav J.S., Chander M.C., and Joshi B.V. Tetrahedron Lett. 29 (1988) 2737-2740
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2737-2740
    • Yadav, J.S.1    Chander, M.C.2    Joshi, B.V.3
  • 21
    • 41349112316 scopus 로고    scopus 로고
    • note
    • 3 by the same sequence. {A figure is presented}
  • 24
    • 41349111890 scopus 로고    scopus 로고
    • note
    • H1-H2 = 4.9 Hz) was used to assign the relative configuration. Acidic methanolysis of 19a afforded the methyl ester 26a, a diastereomer of 21a. {A figure is presented}
  • 25
    • 0030747249 scopus 로고    scopus 로고
    • A chemical correlation was used to assign the absolute configuration of 21a involving its conversion to the optically active sulfonamide (R)-27. In parallel, the known amine 28 was transformed to sulfonamide (S)-27. For the preparation of 28 from d-glyceraldehyde acetonide, see: {A figure is presented}
    • A chemical correlation was used to assign the absolute configuration of 21a involving its conversion to the optically active sulfonamide (R)-27. In parallel, the known amine 28 was transformed to sulfonamide (S)-27. For the preparation of 28 from d-glyceraldehyde acetonide, see:. Badorrey R., Cativiela C., Díaz-de-Villegas M.D., and Gálvez J.A. Synthesis (1997) 747-749 {A figure is presented}
    • (1997) Synthesis , pp. 747-749
    • Badorrey, R.1    Cativiela, C.2    Díaz-de-Villegas, M.D.3    Gálvez, J.A.4
  • 26
    • 41349107403 scopus 로고    scopus 로고
    • note
    • 5SSi: C, 66.52; H, 6.80; N, 2.42. Found: C, 66.27; H, 6.92; N, 2.43.
  • 27
    • 41349093970 scopus 로고    scopus 로고
    • note
    • +): 519.19241. Found: 519.19179.
  • 28
    • 41349105944 scopus 로고    scopus 로고
    • note
    • +): 497.2105. Found: 497.2093.
  • 29
    • 41349105490 scopus 로고    scopus 로고
    • note
    • +): 362.10326. Found: 362.10277.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.