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Volumn 7, Issue 13, 2005, Pages 2583-2585

Chiral Brønsted acid catalyzed enantioselective hydrophosphonylation of imines: Asymmetric synthesis of α-amino phosphonates

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EID: 24044538628     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050695e     Document Type: Article
Times cited : (295)

References (47)
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    • organocatalysis
    • (c) Houk, K. N., List, B., Eds. Special issue on organocatalysis, Acc. Chem. Res. 2004, 37, 487-631.
    • (2004) Acc. Chem. Res. , vol.37 , Issue.SPEC. ISSUE , pp. 487-631
    • Houk, K.N.1    List, B.2
  • 6
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    • organocatalysis
    • (d) List, B., Bolm, C., Eds. Special issue on organocatalysis. Adv. Synth. Catal. 2004, 346, 1021-1249.
    • (2004) Adv. Synth. Catal. , vol.346 , Issue.SPEC. ISSUE , pp. 1021-1249
    • List, B.1    Bolm, C.2
  • 20
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    • Subsequently, similar phosphoric acid catalyzed reactions were reported; see: (a) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356-5357.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356-5357
    • Uraguchi, D.1    Terada, M.2
  • 27
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    • See also references therein
    • (b) Akiyama, T.; Sanada, M.; Fuchibe, K. Synlett 2003, 1463-1464. See also references therein.
    • (2003) Synlett , pp. 1463-1464
    • Akiyama, T.1    Sanada, M.2    Fuchibe, K.3
  • 40
    • 0032562612 scopus 로고    scopus 로고
    • For a review on asymmetric synthesis of organophosphorus compounds, see: Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1279-1332
    • Kolodiazhnyi, O.I.1
  • 41
    • 29944443154 scopus 로고    scopus 로고
    • see ref 10e
    • For a recent example of hydrophosphonylation reaction catalyzed by a chiral thiourea, see ref 10e.
  • 42
    • 29944439448 scopus 로고    scopus 로고
    • note
    • 3)].
  • 43
    • 29944438209 scopus 로고    scopus 로고
    • note
    • The diisopropyl esters gave better results than the corresponding diethyl esters in terms of enantioselectivity, vide infra.
  • 44
    • 29944441354 scopus 로고    scopus 로고
    • note
    • The reaction in m-xylene showed slighly higher enantioselectivity than that in toluene.
  • 45
    • 29944431948 scopus 로고    scopus 로고
    • note
    • The reaction at 0°C took much longer time for completion without beneficial effect on enantioselectivity.
  • 46
    • 29944438739 scopus 로고    scopus 로고
    • note
    • 10d (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.