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Volumn 45, Issue 30, 2004, Pages 5925-5929

Enantioselective Diels-Alder reactions of 3-(acyloxy)acrylates

Author keywords

Acyloxy acrylates; Chiral Lewis acid; Diels Alder

Indexed keywords

3 (ACYLOXY)ACRYLATE; ACRYLIC ACID; COPPER; LEWIS ACID; OXAZOLINE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

EID: 3242804348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.090     Document Type: Article
Times cited : (19)

References (43)
  • 1
    • 0000097153 scopus 로고    scopus 로고
    • Reviews: E.N. Jacobsen, A. Pfaltz, Yamamoto H. New York: Springer
    • Reviews: Evans D.A., Johnson J.S. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. III:1999;1177 Springer, New York
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177
    • Evans, D.A.1    Johnson, J.S.2
  • 15
    • 0001505594 scopus 로고
    • For racemic reactions using β-acyloxy acrylates or equivalents see:
    • For racemic reactions using β-acyloxy acrylates or equivalents see: Martinez-Fresneda P., Vaultier M. Tetrahedron Lett. 30:1989;2929
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2929
    • Martinez-Fresneda, P.1    Vaultier, M.2
  • 25
    • 3242779888 scopus 로고    scopus 로고
    • note
    • 1H NMR (500 or 400 MHz). The relative configuration of endo- and exo-cyclo adducts, endo-7 (R=Me) and exo-7 (R=Me), separated by chromatography on silica gel, were determined by NOESY analysis
  • 26
    • 3242768915 scopus 로고    scopus 로고
    • note
    • 2 (50 mL) was stirred at room temperature for 24 h. Concentration in vacuo followed by chromatography on silica gel (hexane/EtOAc (8:2 to 7:3)) yielded β-acyloxy acrylate
  • 27
    • 3242801042 scopus 로고    scopus 로고
    • note
    • Copper triflate was used as a Lewis acid due to its ready availability in the screening experiments
  • 29
    • 3242755612 scopus 로고    scopus 로고
    • For a review on stereochemical reversal, see:
    • For a review on stereochemical reversal, see: Sibi M.P., Liu M. Curr. Org. Chem. 5:2000;735
    • (2000) Curr. Org. Chem. , vol.5 , pp. 735
    • Sibi, M.P.1    Liu, M.2
  • 31
    • 3242774277 scopus 로고    scopus 로고
    • The reactions utilized the more reactive copper hexafluoroantimonate as the Lewis acid. The absolute configuration shown in table is by analogy based on 5d
  • 38
    • 3242779130 scopus 로고    scopus 로고
    • Ref. 2
    • (d) Ref. 2
  • 40
    • 3242775184 scopus 로고    scopus 로고
    • Ref. 7
    • (f) Ref. 7
  • 43
    • 3242771111 scopus 로고    scopus 로고
    • note
    • We have no crystallographic evidence for this assertion. The complex in principle could also be square-planar. The face selectivity will be the same from either model


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.