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Volumn 8, Issue 4, 2006, Pages 781-784

The Lewis acid-catalyzed Nazarov reaction of 2-(N-methoxycarbonylamino)-1, 4-pentadien-3-ones

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EID: 33644776518     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053071h     Document Type: Article
Times cited : (41)

References (58)
  • 2
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 751-784.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751-784
    • Denmark, S.E.1
  • 20
    • 33644768717 scopus 로고    scopus 로고
    • note
    • 2 is also effective a 1-10 mol %, but the cyclization occurs through a mechanism different from the one reported in Scheme 1.
  • 22
    • 0032511931 scopus 로고    scopus 로고
    • Examples of Lewis acid catalysis have been reported by West in interrupted Nazarov reactions, (b) Giese, S.; West, F. G. Tetrahedron Lett. 1998, 39, 8393-8396.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8393-8396
    • Giese, S.1    West, F.G.2
  • 32
    • 0019808976 scopus 로고
    • For example: streptazolin, streptazon C, and streptazon A, isolated from Streptomyces viridochromogenes, Streptomyces luteogriseus, and FORM5, Strain Al. See: (a) Drautz, H.; Zähner, H.; Kupfer, E.; Keller-Schierlein, W. Helv. Chim. Acta 1981, 64, 1752-1768.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 1752-1768
    • Drautz, H.1    Zähner, H.2    Kupfer, E.3    Keller-Schierlein, W.4
  • 37
    • 4544326574 scopus 로고    scopus 로고
    • and references therein
    • For the synthesis of streptazolin and related natural products see: (f) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329 and references therein.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4327-4329
    • Trost, B.M.1    Chung, C.K.2    Pinkerton, A.B.3
  • 41
    • 33644778245 scopus 로고    scopus 로고
    • note
    • We have already shown that with suitably substituted N-heterocycle derivatives there is an elevated control of the stereochemistry at C5. However, the possibility of organizing the absolute stereochemistry at this carbon atom by an external control is doubtlessly more attractive and general in scope. See refs 4a and 14b,c.
  • 48
    • 0040746033 scopus 로고
    • (E)-Tributyl-1-hexenylstannane 2 was prepared in good yield (82-86%) by Pd-catalyzed hydrostannation of 1-bromohexyne according to two different procedures: (a) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
    • (1990) J. Org. Chem. , vol.55 , pp. 1857-1867
    • Zhang, H.X.1    Guibé, F.2    Balavoine, G.3
  • 51
    • 0037049168 scopus 로고    scopus 로고
    • and references therein
    • Actually, we are aware of no examples of carbonylative Suzuki-Miyaura couplings of alkenylboronic acids, with the exception of a carbonylative reaction of a styrylboronic acid with a diazonium salt. The carbonylative coupling of 9-alkyl-9-BBN, arylboronic acids, and heteroarylboronic acids is instead well-known, and usually requires high temperature and CO pressure, (a) Andrus, M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137-9140 and references therein.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9137-9140
    • Andrus, M.B.1    Ma, Y.2    Zang, Y.3    Song, C.4
  • 52
    • 33644782274 scopus 로고    scopus 로고
    • See ref 21
    • (b) See ref 21.
  • 55
    • 33644767550 scopus 로고    scopus 로고
    • note
    • The water present in mixture with trans-1-hexenylboronic acid can interfere with the catalytic cycle by hydrolyzing the acyl-palladium intermediate complex.
  • 56
    • 0003998388 scopus 로고    scopus 로고
    • A Ready-Reference Book of Chemical and Physical Data, 81st ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL
    • Kerr, J. A. In CRC Handbook of Chemistry and Physics 1999-2000, A Ready-Reference Book of Chemical and Physical Data, 81st ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL 2000.
    • (2000) CRC Handbook of Chemistry and Physics 1999-2000
    • Kerr, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.