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Volumn 5, Issue 15, 2003, Pages 2747-2750

Formal intermolecular 4 + 4 approach to cyclooctanoids: 4 + 3 Capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL COMPOUND; BRIDGED COMPOUND; KETONE DERIVATIVE;

EID: 0141855021     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034985b     Document Type: Article
Times cited : (87)

References (41)
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    • Efficient intermolecular [4 + 3]-cycloadditions of cyclic oxyallyls with reactive cyclic dienes are precedented: (a) Harmata, M.; Bohnert, G. J. Org. Lett. 2003, 5, 59-61. (b) Harmata, M.; Rashatasakhon, P. Org. Lett. 2001, 3, 2533-2525. (c) Leitch, J.; Heise, I. Eur. J. Org. Chem. 2001, 2707-2718. (d) Harmata, M.; Shao, L.; Kürti, L.; Abeywardane, A. Tetrahedron Lett. 1999, 40, 1075-1078. (e) Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217-232. (f) Föhlisch, B.; Joachimi, R. Chem. Ber. 1987, 120, 1951-1960.
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    • note
    • 6 See Supporting Information for a discussion of the structural assignments.
  • 32
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    • For a recent discussion of the theoretical basis of endo/exo preferences in [4 + 3]-cycloadditions, see: Cramer, C. J.; Harmata, M.; Rashatasakhon, P. J. Org. Chem. 2001, 66, 5641-5644.
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    • note
    • Intervention of a competing stepwise cycloaddition mechanism in unsymmetrical cases cannot be ruled out as a possible contributor to the regioselectivity. We thank one of the reviewers for this suggestion.
  • 34
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    • note
    • See Supporting Information for a discussion of the stereochemical assignments of 2c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.