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Volumn 46, Issue 30, 2007, Pages 5737-5740

Construction of tetrahydrofurans by PdII/PdIV- catalyzed aminooxygenation of alkenes

Author keywords

Allylic compounds; Aminopalladation; Oxidation; Palladium; Tetrahydrofurans

Indexed keywords

CARBON; CATALYST ACTIVITY; COVALENT BONDS; OXYGENATION; PALLADIUM; STEREOSELECTIVITY;

EID: 34547480362     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701454     Document Type: Article
Times cited : (261)

References (45)
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    • For a review on the synthetic utility of vicinal amino alcohols, see
    • For a review on the synthetic utility of vicinal amino alcohols, see: S. C. Bergmeier, Tetrahedron 2000, 56, 2561-2576;
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    • β-Hydride elimination remained competitive under all reaction conditions examined
    • β-Hydride elimination remained competitive under all reaction conditions examined.
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    • The modest yield of 2a was due to competitive formation of 2b and competitive decomposition of alcohol 2 to an intractable mixture of oxidation products.
    • The modest yield of 2a was due to competitive formation of 2b and competitive decomposition of alcohol 2 to an intractable mixture of oxidation products.
  • 32
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    • 2 is likely to act as a Lewis acid catalyst for this cyclization rather than to promote a rare 5-endo-trig oxypalladation/acetoxylation sequence.
    • 2 is likely to act as a Lewis acid catalyst for this cyclization rather than to promote a rare 5-endo-trig oxypalladation/acetoxylation sequence.
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    • 4 remains to be definitively elucidated. We speculate that it may render the Pd center more electrophilic and thereby promote coordination of the alcohol.
    • 4 remains to be definitively elucidated. We speculate that it may render the Pd center more electrophilic and thereby promote coordination of the alcohol.
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    • For a rare example of 5-endo-trig oxypalladation, see: S. Saito, T. Hara, N. Takahashi, M. Hirai, T. Moriwake, Synlett 1992, 237-238.
    • For a rare example of 5-endo-trig oxypalladation, see: S. Saito, T. Hara, N. Takahashi, M. Hirai, T. Moriwake, Synlett 1992, 237-238.
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    • 2.
    • 2.
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    • (E)-3 did not form any THF product under these conditions; therefore, the stereochemical outcome of reactions with (Z)-3 appears to reflect a stereospecific transformation of the Z isomer and not isomerization to (E)-3 with subsequent aminocyclization.
    • (E)-3 did not form any THF product under these conditions; therefore, the stereochemical outcome of reactions with (Z)-3 appears to reflect a stereospecific transformation of the Z isomer and not isomerization to (E)-3 with subsequent aminocyclization.
  • 37
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    • The low yield of 3b appears to be due to fast catalyst decomposition under these conditions. The remainder of the material is predominantly (ca. 72%) a mixture of E and Z isomers of 3. See the Supporting Information for a full discussion.
    • The low yield of 3b appears to be due to fast catalyst decomposition under these conditions. The remainder of the material is predominantly (ca. 72%) a mixture of E and Z isomers of 3. See the Supporting Information for a full discussion.
  • 38
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    • For rare examples of cis aminopalladation, see reference [3a] and: a J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689-3692;
    • For rare examples of cis aminopalladation, see reference [3a] and: a) J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689-3692;
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    • Retention of configuration has been observed in some Pd-catalyzed oxidative transformations with CuCl2; for example, see: G. Zhu, S. Ma, X. Lu, Q. Huang, J. Chem. Soc. Chem. Commun. 1995, 271-273
    • 2; for example, see: G. Zhu, S. Ma, X. Lu, Q. Huang, J. Chem. Soc. Chem. Commun. 1995, 271-273.
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    • For examples of oxidative C-O bond formation at Pd that proceed with inversion, see: a J. E. Bäckvall, E. E. Bjoerkman, J. Org. Chem. 1980, 45, 2893-2898;
    • For examples of oxidative C-O bond formation at Pd that proceed with inversion, see: a) J. E. Bäckvall, E. E. Bjoerkman, J. Org. Chem. 1980, 45, 2893-2898;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.