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Volumn 52, Issue 5, 2004, Pages 646-648

Asymmetric Michael reaction promoted by new chiral phase-transfer catalysts

Author keywords

Asymmetric synthesis; Chiral ammonium salt; Michael reaction; Phase transfer catalysis

Indexed keywords

AROMATIC COMPOUND; QUATERNARY AMMONIUM DERIVATIVE;

EID: 16544367097     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.646     Document Type: Article
Times cited : (42)

References (18)
  • 3
    • 0002855131 scopus 로고    scopus 로고
    • ed. by Vogtle F., Soddart J. F., Shibasaki M., Wiley-VCH, Weinheim
    • Rewiews for asymmetric PTC-reactions, see: Shioiri T., Arai S., "Stimulating Concepts in Chemistry," ed. by Vogtle F., Soddart J. F., Shibasaki M., Wiley-VCH, Weinheim, 2000, pp. 123-143.
    • (2000) Stimulating Concepts in Chemistry , pp. 123-143
    • Shioiri, T.1    Arai, S.2
  • 6
    • 0042880949 scopus 로고    scopus 로고
    • and references cited there in
    • Maruoka K., Ooi T., Chem. Rev., 103, 3013-3028 (2003), and references cited there in.
    • (2003) Chem. Rev. , vol.103 , pp. 3013-3028
    • Maruoka, K.1    Ooi, T.2
  • 9
    • 0032560703 scopus 로고    scopus 로고
    • Cinchona alkaloid-derived PTC for asymmetric Michael reaction have been reported, see: Corey E. J., Noe M. C., Xu F., Tetrahedron Lett., 39, 5347-5350 (1998).
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5347-5350
    • Corey, E.J.1    Noe, M.C.2    Xu, F.3
  • 12
    • 0033605033 scopus 로고    scopus 로고
    • Other examples of the asymmetric Michael reaction of using glycine Schiff base and absolute stereochemistry of Michael adducts have been reported, see: Ma D., Cheng K., Tetrahedron Asymmetry, 10, 713-719 (1999).
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 713-719
    • Ma, D.1    Cheng, K.2
  • 16
    • 28244462465 scopus 로고    scopus 로고
    • note
    • 25+92.5° (c=10.0, MeOH).
  • 17
    • 28244500999 scopus 로고    scopus 로고
    • note
    • 4. The solvents were removed in vacuo and subsequent flash column chromatography (hexane: AcOEt=5:1) gave the desired product 8b (39 mg, 100%, 75% ee). The enantiomeric excess was determined by HPLC [CHIRALCEL OD, hexane: i-PrOH=50:1, flow rate: 1.0 ml/min (254 nm), retention times: 7.8 min (minor), 9.1 min (major)].
  • 18
    • 1242338935 scopus 로고    scopus 로고
    • Other type of bis ammonium salt derived from BINOL gave good enantioselectivities in asymmetric Darzens reaction, see: Arai S., Tokumaru K., Aoyama T., Tetrahedron Lett., 45, 1845-1848 (2004).
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1845-1848
    • Arai, S.1    Tokumaru, K.2    Aoyama, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.