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Volumn 48, Issue 7, 2007, Pages 1121-1125

The organocatalytic direct self-trimerization of acrolein: application to the total synthesis of montiporyne F

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; ALDEHYDE DERIVATIVE; CYCLOHEXENE DERIVATIVE; MONTIPORYNE F; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 33846191616     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.055     Document Type: Article
Times cited : (16)

References (120)
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    • note
    • Acrolein is well known to polymerize in prolonged storage or upon exposure to acids or bases.
  • 41
    • 33745211429 scopus 로고    scopus 로고
    • For a recent example of a triple cascade organocatalytic reaction, see:
    • For a recent example of a triple cascade organocatalytic reaction, see:. Enders D., Hüttl M.R.M., Grondal C., and Raabe G. Nature 441 (2006) 861
    • (2006) Nature , vol.441 , pp. 861
    • Enders, D.1    Hüttl, M.R.M.2    Grondal, C.3    Raabe, G.4
  • 42
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    • note
    • See Supplementary data for detail.
  • 43
    • 33846242062 scopus 로고    scopus 로고
    • note
    • Small enantioselectivity were observed in amine-catalyzed self Diels-Alder reactions of α,β-unsaturated ketones, see: Ref. 8.
  • 63
    • 33746311229 scopus 로고    scopus 로고
    • For promising examples of organocatalysis mediated by pyrrolidine and acetic acid, see:
    • For promising examples of organocatalysis mediated by pyrrolidine and acetic acid, see:. McNally A., Evans B., and Gaunt M.J. Angew. Chem., Int. Ed. 45 (2006) 2116
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2116
    • McNally, A.1    Evans, B.2    Gaunt, M.J.3
  • 69
    • 33745825158 scopus 로고    scopus 로고
    • For recent examples in bifunctional organocatalysis, see:
    • For recent examples in bifunctional organocatalysis, see:. Sohtome Y., Hashimoto Y., and Nagasawa K. Eur. J. Org. Chem. (2006) 2894
    • (2006) Eur. J. Org. Chem. , pp. 2894
    • Sohtome, Y.1    Hashimoto, Y.2    Nagasawa, K.3
  • 80
    • 33745683617 scopus 로고    scopus 로고
    • For recent examples in Brønsted acid organocatalysis, see:
    • For recent examples in Brønsted acid organocatalysis, see:. Akiyama T., Itoh J., and Fuchibe K. Adv. Synth. Cat. 348 (2006) 999
    • (2006) Adv. Synth. Cat. , vol.348 , pp. 999
    • Akiyama, T.1    Itoh, J.2    Fuchibe, K.3
  • 99
    • 33846206361 scopus 로고    scopus 로고
    • Acrolein is released into the environment as a product of fermentation and ripening processes. It is a byproduct of lipid peroxidation and was isolated from the wood of oak trees. For references and other examples, see: Slooff, W.; Bont, P. F. H.; Janus, J. A.; Pronk, M. E. J.; Ros, J. P. M. National Institute of Public Health and Environmental Protection, Bilthoven, Report No. 601014001, 1994, Update of the exploratory report: acrolein.
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    • Distillers Co.; German Patent, DE 831,838; 1950.
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    • note
    • Dialdehyde 1 is stable during prolonged storage at ambient temperature, and is inert to some aromatization agents tried, for example, DDQ.
  • 119
    • 33846221838 scopus 로고    scopus 로고
    • note
    • 13C spectra of 2 were identical with the spectra of natural montiporyne F, personal communication with Professor Jee H. Jung, Pusan National University, Korea. The optical rotation and absolute stereochemistry of natural montiporyne F were unknown due to the limited material isolated.
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    • note
    • 9a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.