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Volumn , Issue 7, 2006, Pages 1023-1026

Asymmetric conjugate addition of O-benzylhydroxylamine to α,β-unsaturated 3-acyloxazolidin-2-ones catalyzed by Sc(OTf) 3/i-Pr-pybox complex

Author keywords

Additional reactions; Amino acids; Asymmetric catalyst; Lanthanides; Scandium

Indexed keywords

2,6 BIS(4 ISOPROPYLOXAZOLIN 2 YL)PYRIDINE; 3 ACYLOXAZOLIDIN 2 ONE DERIVATIVE; 3 CROTONOYL 4,4 DIMETHYLOXAZOLIDIN 2 ONE; 3 CROTONOYLOXAZOLIDIN 2 ONE; BENZYLOXYAMINE; BETA AMINO ACID; HYDROXYLAMINE; OXAZOLIDINONE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33646540130     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939068     Document Type: Article
Times cited : (24)

References (77)
  • 1
    • 0001819352 scopus 로고    scopus 로고
    • Lanthanides, Chemistry and Use in Organic Synthesis
    • Kobayashi, S., Ed.; Springer: Heidelberg
    • For reviews, see: (a) Lanthanides, Chemistry and Use in Organic Synthesis, In Topics in Organometallic Chemistry; Kobayashi, S., Ed.; Springer: Heidelberg, 1999.
    • (1999) Topics in Organometallic Chemistry
  • 2
    • 33646567387 scopus 로고    scopus 로고
    • Sc(III) Lewis Acids
    • Yamamoto, H., Ed.; VCH: Weinheim, Chap. 19
    • (b) Kobayashi, S. Sc(III) Lewis Acids, In Lewis Acids in Organic Synthesis, Vol. 2; Yamamoto, H., Ed.; VCH: Weinheim, 2000, Chap. 19.
    • (2000) Lewis Acids in Organic Synthesis , vol.2
    • Kobayashi, S.1
  • 3
    • 0000567965 scopus 로고    scopus 로고
    • Lanthanide Lewis Acids Catalysis
    • Yamamoto, H., Ed.; VCH: Weinheim, Chap. 20
    • (c) Shibasaki, M.; Yamada, K.; Yoshizawa, N. Lanthanide Lewis Acids Catalysis, In Lewis Acids in Organic Synthesis, Vol. 2; Yamamoto, H., Ed.; VCH: Weinheim, 2000, Chap. 20.
    • (2000) Lewis Acids in Organic Synthesis , vol.2
    • Shibasaki, M.1    Yamada, K.2    Yoshizawa, N.3
  • 66
    • 33646544301 scopus 로고    scopus 로고
    • note
    • 14 and the corresponding product, the β-amino-3-acyloxazolidin-2-one derivative, could be easily transformed into more useful compounds.
  • 67
    • 0000157342 scopus 로고    scopus 로고
    • If this reaction was carried out without MS 4 Å, the enantioselectivity of both products decreased [4a; 38% ee (S), 5a; 24% ee (S)]. The effect of molecular sieves has been reported. For examples see: (a) Gothelf, V. K.; Hazell, G. R.; Jørgensen, A. K. J. Org. Chem. 1996, 61, 346.
    • (1996) J. Org. Chem. , vol.61 , pp. 346
    • Gothelf, V.K.1    Hazell, G.R.2    Jørgensen, A.K.3
  • 71
    • 33646537719 scopus 로고    scopus 로고
    • note
    • 3 and i-Pr-pybox at cold temperatures.
  • 72
    • 33646544971 scopus 로고    scopus 로고
    • note
    • 3): δ = 17.7, 37.7, 52.7, 76.3, 77.9, 128.0, 128.3, 128.4, 128.6, 128.7, 129.1, 135.6, 137.3, 169.2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.