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Volumn 62, Issue 40, 2006, Pages 9467-9474

Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; LEWIS ACID; METALLOPORPHYRIN; VINYL DERIVATIVE;

EID: 33747810388     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.051     Document Type: Article
Times cited : (37)

References (70)
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    • Castro, A.M.M.1
  • 5
    • 33747802179 scopus 로고    scopus 로고
    • For some examples of recent leading works on Claisen rearrangement and related reactions, see:
  • 20
    • 33747770791 scopus 로고    scopus 로고
    • For selected works, see:
  • 25
    • 3042539752 scopus 로고    scopus 로고
    • Yamamoto H. (Ed), Oxford, New York, NY Chapter 2
    • Maruoka K. In: Yamamoto H. (Ed). Lewis Acid Reagents (1999), Oxford, New York, NY 5-29 Chapter 2
    • (1999) Lewis Acid Reagents , pp. 5-29
    • Maruoka, K.1
  • 39
    • 0001423835 scopus 로고    scopus 로고
    • For a mechanistic discussion, see:
    • For a mechanistic discussion, see:. Gajewski J.J. Acc. Chem. Res. 30 (1997) 219-225
    • (1997) Acc. Chem. Res. , vol.30 , pp. 219-225
    • Gajewski, J.J.1
  • 41
    • 33747761381 scopus 로고    scopus 로고
    • For some examples of works on Lewis acid-mediated [1,3] rearrangement of allyl vinyl ethers, see:
  • 46
    • 33747772831 scopus 로고    scopus 로고
    • note
    • Yamamoto and Maruoka briefly mentioned in their paper that these bulky organo aluminum-mediated Claisen rearrangements do not entirely proceed through a [3,3] concerted pathway: certain substrates, such as 1-phenyl-2-propenyl vinyl ether 3b, undergo the [1,3] rearrangement in competition to the normal [3,3] Claisen rearrangement (see Refs. 5b,c,e).
  • 48
    • 33747792160 scopus 로고    scopus 로고
    • We have developed porphyrin-based Lewis acid catalysts that can promote regio- and stereoselective isomerization of epoxides to carbonyl compounds, see:
  • 51
    • 33747771837 scopus 로고    scopus 로고
    • Several synthetically useful metalloporphyrin-catalyzed reactions have recently been reported:
  • 59
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    • Jacobsen et al. reported that chromium and manganese salen complexes are useful Lewis acid catalysts for stereoselective ring-opening reactions of epoxides:
    • Jacobsen et al. reported that chromium and manganese salen complexes are useful Lewis acid catalysts for stereoselective ring-opening reactions of epoxides:. Martinez L.E., Leighton J.L., Carsten D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897-5898
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5897-5898
    • Martinez, L.E.1    Leighton, J.L.2    Carsten, D.H.3    Jacobsen, E.N.4
  • 60
    • 33747798132 scopus 로고    scopus 로고
    • note
    • With lower catalyst loading, the rearrangements proceeded with impractically slow rate along with reduced E/Z selectivity. For example, the rearrangement of 1a with 2 mol % of Cr(TPP)Cl under the same reaction conditions did not complete over 24 h to give a 1:1 mixture of E- and Z-2a in 63% yield.
  • 66
    • 33747783695 scopus 로고    scopus 로고
    • note
    • It is well known that simple thermal Claisen rearrangements of aliphatic allyl vinyl ethers are highly stereoselective, leading almost exclusively to the E-configuration of the newly created double bond (see Refs. 1a, 5c, d, and 12).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.