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Volumn 48, Issue 2, 2007, Pages 277-280

A new organocatalyst for 1,3-dipolar cycloadditions of nitrones to α,β-unsaturated aldehydes

Author keywords

3+2 Cycloadditions; Asymmetric catalysis; Diphenyl prolinol; Enantioselectivity; Isoxazolidines; Nitrones; Organocatalysis

Indexed keywords

ALDEHYDE; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

EID: 33845192393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.029     Document Type: Article
Times cited : (89)

References (23)
  • 1
    • 6044269452 scopus 로고    scopus 로고
    • For recent reviews on organocatalysis, see:
    • For recent reviews on organocatalysis, see:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5138-5175
    • Dalko, P.I.1    Moisan, L.2
  • 8
    • 33845223931 scopus 로고    scopus 로고
    • note
    • 4SSi): C, 53.00; H, 6.02; N, 2.96; F, 11.66; S, 6.65; Si, 4.18.
  • 9
    • 33845194912 scopus 로고    scopus 로고
    • A full account of the scope of catalyst 1e has not been reported (Wiener, J. J. M. Ph.D. Thesis, California Institute of Technology, 2004).
  • 10
    • 33845198741 scopus 로고    scopus 로고
    • MacMillan, D. W. C.; Ahrendt, K. A. Chemical synthesis using nonmetallic organic catalyst compositions. PCT Int. Appl., 2001, 81pp. CODEN: PIXXD2 WO 2001053241 A1 20010726 CAN 135:122022 AN 2001:545646.
  • 11
    • 33845208956 scopus 로고    scopus 로고
    • MacMillan, D. W. C. Enantioselective transformations of α,β-unsaturated aldehydes by a wide variety of reactions using imidazolidinone enantiomers as chiral organic catalysts. PCT Int. Appl., 2003, 67pp. CODEN: PIXXD2 WO 2003002491 A2 20030109. Only the 2S,5S configuration of second generation MacMillan catalyst (as a free base) is currently available from Aldrich.
  • 19
    • 33747594792 scopus 로고    scopus 로고
    • Two reports have recently appeared in which they use respectively acetic acid (a) and benzoic acid (b) as additives along with the free base of 1c
    • Two reports have recently appeared in which they use respectively acetic acid (a) and benzoic acid (b) as additives along with the free base of 1c. Wang W., Li H., Wang J., and Zu L. J. Am. Chem. Soc. 128 (2006) 10354-10355
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 10354-10355
    • Wang, W.1    Li, H.2    Wang, J.3    Zu, L.4
  • 21
    • 33845197337 scopus 로고    scopus 로고
    • note
    • 4 (3.0 equiv) in EtOH for ee determination via chiral supercritical fluid chromatography (SFC) using Daicel Chiralcel OD-H or Chiralpak AD-H columns (IPA/hexane, 1.0 mL/min flow rate).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.