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Volumn 17, Issue 10, 2006, Pages 1554-1560

Enantioselective Diels-Alder reaction of o-quinodimethanes by utilizing tartaric acid ester as a chiral auxiliary

Author keywords

[No Author keywords available]

Indexed keywords

DIISOPROPYL TARTRATE; FUMARIC ACID; METHANE; O QUINODIMETHANE; TARTARIC ACID; TARTARIC ACID DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33745400676     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.025     Document Type: Article
Times cited : (17)

References (35)
  • 2
    • 0347596944 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon Press, Oxford
    • Oppolzer W. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford 385-396
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 385-396
    • Oppolzer, W.1
  • 4
    • 0001713702 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon Press, Oxford
    • Durst T., and Breau L. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford 675-697
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 675-697
    • Durst, T.1    Breau, L.2
  • 5
    • 0000486491 scopus 로고
    • The α-hydroxy-o-quinodimethanes were generated by thermal electrocyclic ring-opening reaction of benzocyclobutenols, the photolysis of o-alkylsubstituted benzaldehydes, thermal cheletropic reaction of α-hydroxy dihydrobenzothiophene dioxides, and 1,4-elimination from o-(α-stannylmethyl)benzaldehydes. Examples from benzocyclobutenols:
    • The α-hydroxy-o-quinodimethanes were generated by thermal electrocyclic ring-opening reaction of benzocyclobutenols, the photolysis of o-alkylsubstituted benzaldehydes, thermal cheletropic reaction of α-hydroxy dihydrobenzothiophene dioxides, and 1,4-elimination from o-(α-stannylmethyl)benzaldehydes. Examples from benzocyclobutenols:. Choy W., and Yang H. J. Org. Chem. 53 (1988) 5796-5798
    • (1988) J. Org. Chem. , vol.53 , pp. 5796-5798
    • Choy, W.1    Yang, H.2
  • 10
    • 0000494577 scopus 로고
    • from α-hydroxy dihydrobenzothiophene dioxides:
    • from α-hydroxy dihydrobenzothiophene dioxides:. Charlton J.L., Koh K., and Plourde G.L. Tetrahedron Lett. 30 (1989) 3279-3282
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3279-3282
    • Charlton, J.L.1    Koh, K.2    Plourde, G.L.3
  • 18
    • 33745382707 scopus 로고    scopus 로고
    • Sano, H.; Shi, Y.; Kosugi, M. 85th National Meeting of the Chemical Society of Japan, Yokohama, 2005; Abstract 2PC-002.
  • 21
    • 33745395400 scopus 로고    scopus 로고
    • Kobayashi S., and Jørgensen K.A. (Eds), Wiley-VCH, Weinheim Chapter 1
    • Hayashi Y. In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reaction in Organic Synthesis (2002), Wiley-VCH, Weinheim Chapter 1
    • (2002) Cycloaddition Reaction in Organic Synthesis
    • Hayashi, Y.1
  • 23
    • 33745387191 scopus 로고    scopus 로고
    • Kobayashi S., and Jørgensen K.A. (Eds), Wiley-VCH, Weinheim Chapter 5
    • Kobayashi S. In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reaction in Organic Synthesis (2002), Wiley-VCH, Weinheim Chapter 5
    • (2002) Cycloaddition Reaction in Organic Synthesis
    • Kobayashi, S.1
  • 33
    • 33745392750 scopus 로고    scopus 로고
    • note
    • When the zinc alkoxide was formed completely by the reaction of benzocyclobutenol 1A and the reactive isopropylzinc reagent for an appropriate reaction time, the enantioselectivity might be enhanced.
  • 34
    • 33745380905 scopus 로고    scopus 로고
    • note
    • When the interval without a dienophile was too long, the production of a slight amount of a by-product 12, which might have disturbed the ideal reaction pathway, was confirmed. Although the mechanism of the production of 12 was not clear yet, a possible pathway is shown in the following scheme.{A figure is presented}
  • 35
    • 33745408003 scopus 로고    scopus 로고
    • note
    • Supplementary material of Ref. 2d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.