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Volumn 10, Issue 3, 2008, Pages 437-440

Sequential Rh(l)/Pd-catalyzed 1,4-addition/Lntramolecular allylation: Stereocontrolled construction of γ-butyrolactones and cyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; LACTONE; PALLADIUM; RHODIUM;

EID: 38949130047     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702613f     Document Type: Article
Times cited : (42)

References (43)
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    • For a review on Rh(I)-catalyzed conjugate additions, see: Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
    • (c) For a review on Rh(I)-catalyzed conjugate additions, see: Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
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    • To date, a single asymmetric example has been reported, see
    • To date, a single asymmetric example has been reported, see: Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508-11509.
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    • Asymmetric synthesis of all-carbon quaternary centers from alkylidene Meldrum's acids via Cu-catalyzed conjugate addition of dialkylzinc reagents, see
    • Asymmetric synthesis of all-carbon quaternary centers from alkylidene Meldrum's acids via Cu-catalyzed conjugate addition of dialkylzinc reagents, see: Fillion, E.; Wilsily, A. J. Am. Chem. Soc. 2006, 128, 2774-2775.
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    • The conversion was >99% in all cases
    • The conversion was >99% in all cases.
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    • 4. An 86% yield of 4m was obtained with 6 mol % of Rh at rt for 15 h.
    • 4. An 86% yield of 4m was obtained with 6 mol % of Rh at rt for 15 h.
  • 13
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    • Intermolecular C-allylation of Meldrum's acids with π-allylpalladium complexes: (a) Trost, B. M.; Brennan, M. K. Org. Lett. 2007, 9, 3961-3964.
    • Intermolecular C-allylation of Meldrum's acids with π-allylpalladium complexes: (a) Trost, B. M.; Brennan, M. K. Org. Lett. 2007, 9, 3961-3964.
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    • Meldrum's acid C- and O-dialkylation: Snyder, C. A.; Selegue, J. P.; Dosunmu, E.; Tice, N. C.; Parkin, S. J. Org. Chem. 2003, 68, 7455-7459.
    • Meldrum's acid C- and O-dialkylation: Snyder, C. A.; Selegue, J. P.; Dosunmu, E.; Tice, N. C.; Parkin, S. J. Org. Chem. 2003, 68, 7455-7459.
  • 17
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    • The Pd-catalyzed synthesis of vinylcyclopropanes via intramolecular C-allylation of malonate derivatives with π-allylpalladium complexes has been reported; see: (a) Bäckvall, J. E, Vågberg, J. O, Zercher, C, Genêt, J.-P, Denis, A. J. Org. Chem. 1987, 52, 5430-5435
    • The Pd-catalyzed synthesis of vinylcyclopropanes via intramolecular C-allylation of malonate derivatives with π-allylpalladium complexes has been reported; see: (a) Bäckvall, J. E.; Vågberg, J. O.; Zercher, C.; Genêt, J.-P.; Denis, A. J. Org. Chem. 1987, 52, 5430-5435.
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    • The formation of 8 from 4a in the absence of excess alcohol may be attributed to the interception of the acylketene by the actetate formed in the course of the reaction. The resulting anhydride is then hydrolyzed in the workup with concommitent decarboxylation.
    • The formation of 8 from 4a in the absence of excess alcohol may be attributed to the interception of the acylketene by the actetate formed in the course of the reaction. The resulting anhydride is then hydrolyzed in the workup with concommitent decarboxylation.
  • 23
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    • 1H NMR spectra of the crude reaction mixtures.
    • 1H NMR spectra of the crude reaction mixtures.
  • 24
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    • Attempts to generate the π-allylrhodium complex by modifying the catalyst in situ by the addition of P(OEt>3 failed; see: (a) Evans, P. A, Robinson, J. E, Moffett, K. K. Org. Lett. 2001, 3, 3269-3271
    • Attempts to generate the π-allylrhodium complex by modifying the catalyst in situ by the addition of P(OEt>3 failed; see: (a) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269-3271.
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    • 1H NMR spectra of the crude mixture.
    • 1H NMR spectra of the crude mixture.
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    • C-Allylation of stannyl ketone enolates with Pd(II) π-allyl complexes was reported; see: (a) Trost, B. M.; Schroeder, G. M. Chem. Eur. J. 2005, 11, 174-184.
    • C-Allylation of stannyl ketone enolates with Pd(II) π-allyl complexes was reported; see: (a) Trost, B. M.; Schroeder, G. M. Chem. Eur. J. 2005, 11, 174-184.
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    • Unfortunately, the addition of both catalysts at the beginning of the domino reaction failed
    • Unfortunately, the addition of both catalysts at the beginning of the domino reaction failed.
  • 33
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    • It is postulated that decarboxylation to 8 is promoted by tributyltin species in combination with TBAB.
    • It is postulated that decarboxylation to 8 is promoted by tributyltin species in combination with TBAB.
  • 37
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    • For a review on the stereoselective synthesis of cyclopropanes, see
    • (b) For a review on the stereoselective synthesis of cyclopropanes, see: Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
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    • 3 to form byproduct 6c.
    • 3 to form byproduct 6c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.