메뉴 건너뛰기




Volumn 74, Issue 5, 2009, Pages 1876-1885

New strategies for protecting group chemistry: Synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ETHERS; NEW STRATEGIES; OXIDATIVE CLEAVAGES; PROTECTING GROUPS;

EID: 64249164710     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802229p     Document Type: Article
Times cited : (15)

References (63)
  • 2
  • 3
    • 0842285267 scopus 로고    scopus 로고
    • Mickel, et al, S. J. Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1: Synthetic Strategy and Preparation of a Common Precursor. Org. Process Res. Dev. 2004, 8, 92-100. Part 2: Synthesis of Fragments C1-6 and C9-14, 101-106. Part 3: Synthesis of Fragment C15-21, 107-112. Part 4: Preparation of Fragment C7-24, 113-121. Part 5: Linkage of Fragments C1-6 and C7-24 and finale, 122-130.
    • Mickel, et al, S. J. Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1: Synthetic Strategy and Preparation of a Common Precursor. Org. Process Res. Dev. 2004, 8, 92-100. Part 2: Synthesis of Fragments C1-6 and C9-14, 101-106. Part 3: Synthesis of Fragment C15-21, 107-112. Part 4: Preparation of Fragment C7-24, 113-121. Part 5: Linkage of Fragments C1-6 and C7-24 and finale, 122-130.
  • 4
    • 0004288915 scopus 로고    scopus 로고
    • Hanessian, S, Ed, Marcel Dekker: New York
    • (a) Preparative Carbohydrate Chemistry; Hanessian, S. , Ed.; Marcel Dekker: New York, 1997.
    • (1997) Preparative Carbohydrate Chemistry
  • 5
    • 33751021311 scopus 로고    scopus 로고
    • Levy, D. E, Fügedi, P, Eds, Taylor & Francis: Boca Raton, FL
    • (b) The Organic Chemistry of Sugars; Levy, D. E., Fügedi, P., Eds.; Taylor & Francis: Boca Raton, FL, 2006.
    • (2006) The Organic Chemistry of Sugars
  • 6
    • 0037667047 scopus 로고    scopus 로고
    • Large-Scale Manufacture of Peptide Therapeutics by Chemical Synthesis
    • Bray, B. L. Large-Scale Manufacture of Peptide Therapeutics by Chemical Synthesis. Nat. Rev. Drug Discovery 2003, 2, 587-593.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 587-593
    • Bray, B.L.1
  • 8
    • 0034718086 scopus 로고    scopus 로고
    • Plante, O.; Buchwald, S. L.; Seeberger, P. H. Halobenzyl Ethers As Protecting Groups for Organic Synthesis. J. Am. Chem. Soc. 2000, 122, 7148-7149.
    • Plante, O.; Buchwald, S. L.; Seeberger, P. H. Halobenzyl Ethers As Protecting Groups for Organic Synthesis. J. Am. Chem. Soc. 2000, 122, 7148-7149.
  • 9
    • 0036427428 scopus 로고    scopus 로고
    • Convergent Synthesis of the BCDE-Ring Part of Ciguatoxin
    • Fujiwara, K.; Koyama, Y.; Kawai, K.; Tanaka, H.; Murai, A. Convergent Synthesis of the BCDE-Ring Part of Ciguatoxin. Synlett 2002, 1835-1838.
    • (2002) Synlett , pp. 1835-1838
    • Fujiwara, K.1    Koyama, Y.2    Kawai, K.3    Tanaka, H.4    Murai, A.5
  • 10
    • 0033597612 scopus 로고    scopus 로고
    • Jobron, L.; Hindsgaul, O. Novel Para-Substituted Benzyl Ethers for Hydroxyl Group Protection. J. Am. Chem. Soc. 1999, 121, 5835-5836.
    • Jobron, L.; Hindsgaul, O. Novel Para-Substituted Benzyl Ethers for Hydroxyl Group Protection. J. Am. Chem. Soc. 1999, 121, 5835-5836.
  • 11
    • 33845280670 scopus 로고
    • Armed" and "Disarmed" N-Pentenyl Glycosides in Saccharide Couplings Leading to Oligosaccharides
    • Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. "Armed" and "Disarmed" N-Pentenyl Glycosides in Saccharide Couplings Leading to Oligosaccharides. J. Am. Chem. Soc. 1988, 110, 5583-5584.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 5583-5584
    • Mootoo, D.R.1    Konradsson, P.2    Udodong, U.3    Fraser-Reid, B.4
  • 12
    • 0346150287 scopus 로고    scopus 로고
    • Oxidation of Carbon-Silicon Bonds: The Dramatic Advantage of Strained Siletanes
    • Sunderhaus, J. D.; Lam, H.; Dudley, G. B. Oxidation of Carbon-Silicon Bonds: The Dramatic Advantage of Strained Siletanes. Org. Lett. 2003, 5, 4571-4573.
    • (2003) Org. Lett , vol.5 , pp. 4571-4573
    • Sunderhaus, J.D.1    Lam, H.2    Dudley, G.B.3
  • 13
    • 0002437012 scopus 로고    scopus 로고
    • Oxidative Cleavage of the Carbon-Silicon Bond: Development, Mechanism, Scope, and Limitations
    • Larson, G. L, Ed, JAI Press: Greenwich, CT
    • Tamao, K. Oxidative Cleavage of the Carbon-Silicon Bond: Development, Mechanism, Scope, and Limitations. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 1-62.
    • (1996) Advances in Silicon Chemistry , vol.3 , pp. 1-62
    • Tamao, K.1
  • 14
    • 0030007621 scopus 로고    scopus 로고
    • The Oxidation of the Carbon-Silicon Bond
    • Jones, G. R.; Landais, Y. The Oxidation of the Carbon-Silicon Bond. Tetrahedron 1996, 52, 7599-7662.
    • (1996) Tetrahedron , vol.52 , pp. 7599-7662
    • Jones, G.R.1    Landais, Y.2
  • 15
    • 84906448432 scopus 로고    scopus 로고
    • Four-Membered Rings with One Silicon, Germanium, Tin, or Lead Atom
    • For a review of the chemistry of organosiletanes see:, Katritsky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Eds, Elsevier: Oxford, U.K
    • For a review of the chemistry of organosiletanes see: Kozytska, M. V.; Dudley, G. B. Four-Membered Rings with One Silicon, Germanium, Tin, or Lead Atom. In Comprehensive Heterocyclic Chemistry III; Katritsky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, U.K., 2008; Vol 2, pp 513-554.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.2 , pp. 513-554
    • Kozytska, M.V.1    Dudley, G.B.2
  • 16
    • 0002994601 scopus 로고
    • Nucleophilic Hydroxymethylation of Carbonyl Compounds: 1-(Hydroxymethyl)cyclohexanol
    • Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Nucleophilic Hydroxymethylation of Carbonyl Compounds: 1-(Hydroxymethyl)cyclohexanol. Org. Synth. 1990, 69, 96-105.
    • (1990) Org. Synth , vol.69 , pp. 96-105
    • Tamao, K.1    Ishida, N.2    Ito, Y.3    Kumada, M.4
  • 17
    • 0001782321 scopus 로고    scopus 로고
    • Silyl-to-Hydroxy Conversion in Organic Synthesis
    • Fleming, I. Silyl-to-Hydroxy Conversion in Organic Synthesis. Chemtracts: Org. Chem. 1996, 1-64.
    • (1996) Chemtracts: Org. Chem , pp. 1-64
    • Fleming, I.1
  • 18
    • 17144427669 scopus 로고    scopus 로고
    • Lam, H.; House, S. E.; Dudley, G. B. the Para-Siletanylbenzyl (PSB) Ether: A Peroxide-Cleavable Protecting Group for Alcohols and Phenols. Tetrahedron Lett. 2005, 46, 3283-3285.
    • Lam, H.; House, S. E.; Dudley, G. B. the Para-Siletanylbenzyl (PSB) Ether: A Peroxide-Cleavable Protecting Group for Alcohols and Phenols. Tetrahedron Lett. 2005, 46, 3283-3285.
  • 19
    • 0027403105 scopus 로고
    • A Useful Application of Benzyl Trichloroacetimidate for the Benzylation of Alcohols
    • Eckenberg, P.; Groth, U.; Huhn, T.; Richter, N.; Schmeck, C. A Useful Application of Benzyl Trichloroacetimidate for the Benzylation of Alcohols. Tetrahedron 1993, 49, 1619-1624.
    • (1993) Tetrahedron , vol.49 , pp. 1619-1624
    • Eckenberg, P.1    Groth, U.2    Huhn, T.3    Richter, N.4    Schmeck, C.5
  • 21
    • 34047222695 scopus 로고    scopus 로고
    • Synthesis of Water-Dispersible, Fluorinated Particles with Grafting Sulfonate Chains by the Core Crosslinking of Block Copolymer Micelles
    • Matsumoto, K.; Kage, S.; Matsuoka, H. Synthesis of Water-Dispersible, Fluorinated Particles with Grafting Sulfonate Chains by the Core Crosslinking of Block Copolymer Micelles. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1316-1323.
    • (2007) J. Polym. Sci., Part A: Polym. Chem , vol.45 , pp. 1316-1323
    • Matsumoto, K.1    Kage, S.2    Matsuoka, H.3
  • 22
    • 0035913011 scopus 로고    scopus 로고
    • Sheikh, R. K.; Tharanikkarasu, K.; Imae, I.; Kawakami, Y. Silacyclobutane As Carbanion Pump in Anionic Polymerization. 2. Effective Trapping of the Initially Formed Carbanion by Diphenylethylene. Macromolecules 2001, 34, 4384-4389.
    • Sheikh, R. K.; Tharanikkarasu, K.; Imae, I.; Kawakami, Y. Silacyclobutane As "Carbanion Pump" in Anionic Polymerization. 2. Effective Trapping of the Initially Formed Carbanion by Diphenylethylene. Macromolecules 2001, 34, 4384-4389.
  • 23
    • 0034991112 scopus 로고    scopus 로고
    • The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives
    • For a systematic study of protodesilylation of various arylsilanes, see
    • For a systematic study of protodesilylation of various arylsilanes, see: Utimoto, K.; Otake, Y.; Yoshino, H.; Kuwahara, E.; Oshima, K.; Matsubara, S. The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives. Bull. Chem. Soc. Jpn. 2001, 74, 753-754.
    • (2001) Bull. Chem. Soc. Jpn , vol.74 , pp. 753-754
    • Utimoto, K.1    Otake, Y.2    Yoshino, H.3    Kuwahara, E.4    Oshima, K.5    Matsubara, S.6
  • 24
    • 29744438054 scopus 로고    scopus 로고
    • A Bench-Stable Organic Salt for the Benzylation of Alcohols
    • Poon, K. W. C.; House, S. E.; Dudley, G. B. A Bench-Stable Organic Salt for the Benzylation of Alcohols. Synlett 2005, 3142-3144.
    • (2005) Synlett , pp. 3142-3144
    • Poon, K.W.C.1    House, S.E.2    Dudley, G.B.3
  • 25
    • 0007706809 scopus 로고
    • Phase-Transfer Mediated Heteroaromatic Nucleophilic Substitution: Introduction of a β-Adrenergic Blocking Moiety
    • Serio Duggan, A. J.; Grabowski, E. J. J.; Russ, W. K. Phase-Transfer Mediated Heteroaromatic Nucleophilic Substitution: Introduction of a β-Adrenergic Blocking Moiety. Synthesis 1980, 573-575.
    • (1980) Synthesis , pp. 573-575
    • Serio Duggan, A.J.1    Grabowski, E.J.J.2    Russ, W.K.3
  • 26
    • 83455255052 scopus 로고    scopus 로고
    • 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate
    • Paquette, L, Fuchs, P, Crich, D, Molander, G, Eds, John Wiley & Sons: Chichester, U.K, DOI: 10.1002/047084289X.rn00906
    • Dudley, G. B. 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate. In Electronic Encylopedia of Reagents for Organic Synthesis; Paquette, L., Fuchs, P., Crich, D., Molander, G., Eds.; John Wiley & Sons: Chichester, U.K., DOI: 10.1002/047084289X.rn00906.
    • Electronic Encylopedia of Reagents for Organic Synthesis
    • Dudley, G.B.1
  • 27
    • 33646520636 scopus 로고    scopus 로고
    • Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt
    • Poon, K. W. C.; Dudley, G. B. Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt. J. Org. Chem. 2006, 71, 3923-3927.
    • (2006) J. Org. Chem , vol.71 , pp. 3923-3927
    • Poon, K.W.C.1    Dudley, G.B.2
  • 28
    • 85026873969 scopus 로고    scopus 로고
    • Protection of Alcohols Using 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-Methyl Propanoate
    • Poon, K. W. C.; Albiniak, P. A.; Dudley, G. B. Protection of Alcohols Using 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-Methyl Propanoate. Org. Synth. 2007, 84, 295-305.
    • (2007) Org. Synth , vol.84 , pp. 295-305
    • Poon, K.W.C.1    Albiniak, P.A.2    Dudley, G.B.3
  • 29
    • 64249113411 scopus 로고    scopus 로고
    • Dudley Benzylation Reagent. ChemFiles 2007, 7 (3), 3. Sigma-Aldrich product number: 679674.
    • Dudley Benzylation Reagent. ChemFiles 2007, 7 (3), 3. Sigma-Aldrich product number: 679674.
  • 30
    • 33947634131 scopus 로고    scopus 로고
    • A Method for the Synthesis of Para-Methoxybenzyl (PMB) Ethers Under Effectively Neutral Conditions
    • Nwoye, E. O.; Dudley, G. B. A Method for the Synthesis of Para-Methoxybenzyl (PMB) Ethers Under Effectively Neutral Conditions. Chem. Commun. 2007, 1436-1437.
    • (2007) Chem. Commun , pp. 1436-1437
    • Nwoye, E.O.1    Dudley, G.B.2
  • 31
    • 39349091263 scopus 로고    scopus 로고
    • An Efficient Means for Generating P-Methoxybenzyl (PMB) Ethers under Mildly Acidic Conditions
    • Stewart, C. A.; Peng, X.; Paquette, L. A. An Efficient Means for Generating P-Methoxybenzyl (PMB) Ethers under Mildly Acidic Conditions. Synthesis 2008, 433-437.
    • (2008) Synthesis , pp. 433-437
    • Stewart, C.A.1    Peng, X.2    Paquette, L.A.3
  • 32
    • 64249093719 scopus 로고    scopus 로고
    • Also now commercially available: Sigma-Aldrich product number 701440.
    • Also now commercially available: Sigma-Aldrich product number 701440.
  • 34
    • 0343643766 scopus 로고
    • 2-Chloro-1-Methylpyridinium Iodide
    • Paquette, L. A, Ed, John Wiley and Sons: New York, New York
    • Armstrong, A. 2-Chloro-1-Methylpyridinium Iodide. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: New York, New York, 1995; Vol. 2, pp 1174-1175.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.2 , pp. 1174-1175
    • Armstrong, A.1
  • 35
    • 0007511516 scopus 로고
    • New Synthetic Reactions Based on the Onium Salts of Aza-Arenes
    • Mukaiyama, T. New Synthetic Reactions Based on the Onium Salts of Aza-Arenes. Angew. Chem., Int. Ed. Engl. 1979, 18, 707-721.
    • (1979) Angew. Chem., Int. Ed. Engl , vol.18 , pp. 707-721
    • Mukaiyama, T.1
  • 36
    • 31144454147 scopus 로고    scopus 로고
    • P- iletanylbenzylidene Acetal: Oxidizable Protecting Group for Diols
    • House, S. E.; Poon, K. W. C.; Lam, H.; Dudley, G. B. P- iletanylbenzylidene Acetal: Oxidizable Protecting Group for Diols. J. Org. Chem. 2006, 71, 420-422.
    • (2006) J. Org. Chem , vol.71 , pp. 420-422
    • House, S.E.1    Poon, K.W.C.2    Lam, H.3    Dudley, G.B.4
  • 37
    • 37549039126 scopus 로고    scopus 로고
    • Nitrone [2 + 3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor: (-)-Omuralide
    • Legeay, J.-C.; Langlois, L. Nitrone [2 + 3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor: (-)-Omuralide. J. Org. Chem. 2007, 72, 10108-10113.
    • (2007) J. Org. Chem , vol.72 , pp. 10108-10113
    • Legeay, J.-C.1    Langlois, L.2
  • 38
    • 33845465260 scopus 로고    scopus 로고
    • Stereoselective Formal Synthesis of the Potent Proteasome Inhibitor: Salinosporamide A
    • Caubert, V.; Masse', J.; Retailleau, P.; Langlois, N. Stereoselective Formal Synthesis of the Potent Proteasome Inhibitor: Salinosporamide A. Tetrahedron Lett. 2007, 48, 381-384.
    • (2007) Tetrahedron Lett , vol.48 , pp. 381-384
    • Caubert, V.1    Masse', J.2    Retailleau, P.3    Langlois, N.4
  • 40
    • 44949231054 scopus 로고    scopus 로고
    • Catalyst-Dependent Syntheses of Phosphatidylinositol-5-Phosphate-Dic8 and Its Enantiomer
    • Kayser-Bricker, K. J.; Jordan, P. A.; Miller, S. J. Catalyst-Dependent Syntheses of Phosphatidylinositol-5-Phosphate-Dic8 and Its Enantiomer. Tetrahedron 2008, 64, 7015-7120.
    • (2008) Tetrahedron , vol.64 , pp. 7015-7120
    • Kayser-Bricker, K.J.1    Jordan, P.A.2    Miller, S.J.3
  • 41
    • 35948952320 scopus 로고    scopus 로고
    • Synthesis of Benzyl Esters Using 2-Benzyloxy-1-Methylpyridinium Triflate
    • Tummatorn, J.; Albiniak, P. A.; Dudley, G. B. Synthesis of Benzyl Esters Using 2-Benzyloxy-1-Methylpyridinium Triflate. J. Org. Chem. 2007, 72, 8962-8964.
    • (2007) J. Org. Chem , vol.72 , pp. 8962-8964
    • Tummatorn, J.1    Albiniak, P.A.2    Dudley, G.B.3
  • 42
    • 0000080248 scopus 로고    scopus 로고
    • Oxidation of Sterically Hindered Alkoxysilanes and Phenylsilanes under Basic Conditions
    • Smitrovich, J. H.; Woerpel, K. A. Oxidation of Sterically Hindered Alkoxysilanes and Phenylsilanes under Basic Conditions. J. Org. Chem. 1996, 61, 6044-6046.
    • (1996) J. Org. Chem , vol.61 , pp. 6044-6046
    • Smitrovich, J.H.1    Woerpel, K.A.2
  • 43
    • 0038441400 scopus 로고    scopus 로고
    • Zirconium(IV) Chloride Catalyzed New and Efficient Protocol for the Selective Cleavage of P-Methoxybenzyl Ethers
    • Sharma, G. V. M.; Reddy, C. G.; Krishna, P. R. Zirconium(IV) Chloride Catalyzed New and Efficient Protocol for the Selective Cleavage of P-Methoxybenzyl Ethers. J. Org. Chem. 2003, 68, 4574-4575.
    • (2003) J. Org. Chem , vol.68 , pp. 4574-4575
    • Sharma, G.V.M.1    Reddy, C.G.2    Krishna, P.R.3
  • 44
    • 84982373258 scopus 로고
    • Tertiary Phosphane/Tetrachloromethane, A Versatile Reagent for Chlorination, Dehydration, And P-N Linkage
    • Appel, R. Tertiary Phosphane/Tetrachloromethane, A Versatile Reagent for Chlorination, Dehydration, And P-N Linkage. Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811.
    • (1975) Angew. Chem., Int. Ed. Engl , vol.14 , pp. 801-811
    • Appel, R.1
  • 45
    • 64249116134 scopus 로고    scopus 로고
    • Multiple attempts to prepare Grignard 55 using activated magnesium turnings under standard conditions were unsuccessful. Insertion does not occur at room temperature, and it appears as though magnesium insertion into the benzylic carbon-oxygen bond occurs upon prolonged heating, based on recovery of bis-siletane 56 from the crude reaction mixture.
    • Multiple attempts to prepare Grignard 55 using activated magnesium turnings under standard conditions were unsuccessful. Insertion does not occur at room temperature, and it appears as though magnesium insertion into the benzylic carbon-oxygen bond occurs upon prolonged heating, based on recovery of bis-siletane 56 from the crude reaction mixture.
  • 46
    • 33746657188 scopus 로고    scopus 로고
    • Mild Iodine-Magnesium Exchange of Iodoaromatics Bearing a Pyrimidine Ring with Isopropylmagnesium Chloride
    • Wang, X.-j.; Xu, Y.; Zhang, L.; Krishnamurthy, D.; Senanayake, C. H. Mild Iodine-Magnesium Exchange of Iodoaromatics Bearing a Pyrimidine Ring with Isopropylmagnesium Chloride. Org. Lett. 2006, 8, 3141-3144.
    • (2006) Org. Lett , vol.8 , pp. 3141-3144
    • Wang, X.-J.1    Xu, Y.2    Zhang, L.3    Krishnamurthy, D.4    Senanayake, C.H.5
  • 49
    • 84869275292 scopus 로고    scopus 로고
    • Note that the Sigma-Aldrich list price of siletane 28 (catalog number: 411582-5g, list price: $145.50, $3.54/mmol) is comparable to that of TBS-OTf (catalog number: 226149-5g, list price: $52.60, $2.78/mmol); see http:// www.sigmaaldrich.com.
    • Note that the Sigma-Aldrich list price of siletane 28 (catalog number: 411582-5g, list price: $145.50, $3.54/mmol) is comparable to that of TBS-OTf (catalog number: 226149-5g, list price: $52.60, $2.78/mmol); see http:// www.sigmaaldrich.com.
  • 51
    • 0033009793 scopus 로고    scopus 로고
    • 2 As an Initiator. Synth. Commun. 1999, 29, 1037-1039.
    • 2 As an Initiator. Synth. Commun. 1999, 29, 1037-1039.
  • 52
    • 0034671743 scopus 로고    scopus 로고
    • Transition Metal Catalyzed Preparation of Grignard Compounds
    • Bogdanovic, B.; Schwickardi, M. Transition Metal Catalyzed Preparation of Grignard Compounds. Angew. Chem., Int. Ed. 2000, 39, 4610-4612.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 4610-4612
    • Bogdanovic, B.1    Schwickardi, M.2
  • 53
    • 64249133265 scopus 로고    scopus 로고
    • Grignard formation does not initiate spontaneously even when using magnesium turnings that were preactivated with iodine and/or dibromoethane
    • Grignard formation does not initiate spontaneously even when using magnesium turnings that were preactivated with iodine and/or dibromoethane.
  • 54
    • 64249121190 scopus 로고    scopus 로고
    • A reflux condenser was included in the experimental setup as a precaution; solvent reflux was never definitively observed in this experiment
    • A reflux condenser was included in the experimental setup as a precaution; solvent reflux was never definitively observed in this experiment.
  • 55
    • 64249130471 scopus 로고    scopus 로고
    • The authors thank Ms. Cecelia C. O'Leary, an undergraduate research student in the Dudley Lab, for providing independent verification of this new and unusual procedure for making Grignard reagents. Further exploration of this protocol is underway and will be reported in due course
    • The authors thank Ms. Cecelia C. O'Leary, an undergraduate research student in the Dudley Lab, for providing independent verification of this new and unusual procedure for making Grignard reagents. Further exploration of this protocol is underway and will be reported in due course.
  • 56
    • 0036798587 scopus 로고    scopus 로고
    • Design and Implementation of New, Silicon-Based, Cross-Coupling Reactions: Importance of Silicon-Oxygen Bonds
    • and references cited
    • Denmark, S. E.; Sweis, R. F. Design and Implementation of New, Silicon-Based, Cross-Coupling Reactions: Importance of Silicon-Oxygen Bonds. Acc. Chem. Res. 2002, 35, 835-846, and references cited.
    • (2002) Acc. Chem. Res , vol.35 , pp. 835-846
    • Denmark, S.E.1    Sweis, R.F.2
  • 57
    • 0000019167 scopus 로고
    • Chemistry of Enoxysilacyclobutanes: Highly Selective Uncatalvzed Aldol Additions
    • Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. Chemistry of Enoxysilacyclobutanes: Highly Selective Uncatalvzed Aldol Additions. J. Am. Chem. Soc. 1994, 116, 7026-7043.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 7026-7043
    • Denmark, S.E.1    Griedel, B.D.2    Coe, D.M.3    Schnute, M.E.4
  • 58
    • 59849101603 scopus 로고    scopus 로고
    • Palladium-Catalyzed Formal Cycloaddition of Silacyclobutanes with Enones: Synthesis of Eight-Membered Cyclic Silyl Enolates
    • Hirano, K.; Yorimitsu, H.; Oshima, K. Palladium-Catalyzed Formal Cycloaddition of Silacyclobutanes with Enones: Synthesis of Eight-Membered Cyclic Silyl Enolates. Org. Lett. 2008, 10, 2199-2201.
    • (2008) Org. Lett , vol.10 , pp. 2199-2201
    • Hirano, K.1    Yorimitsu, H.2    Oshima, K.3
  • 59
    • 34249023288 scopus 로고    scopus 로고
    • Nickel-Catalyzed Regio- And Stereoselective Silylation of Terminal Alkenes with Silacyclobutanes: Facile Access to Vinylsilanes from Alkenes
    • Hirano, K.; Yorimitsu, H.; Oshima, K. Nickel-Catalyzed Regio- And Stereoselective Silylation of Terminal Alkenes with Silacyclobutanes: Facile Access to Vinylsilanes from Alkenes. J. Am. Chem. Soc. 2007, 129, 6094-6095.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6094-6095
    • Hirano, K.1    Yorimitsu, H.2    Oshima, K.3
  • 60
    • 32644446485 scopus 로고    scopus 로고
    • Nickel-Catalyzed Reactions of Silacyclobutanes with Aldehydes: Ring Opening and Ring Expansion Reaction
    • Hirano, K.; Yorimitsu, H.; Oshima, K. Nickel-Catalyzed Reactions of Silacyclobutanes with Aldehydes: Ring Opening and Ring Expansion Reaction. Org. Lett. 2006, 8, 483-485.
    • (2006) Org. Lett , vol.8 , pp. 483-485
    • Hirano, K.1    Yorimitsu, H.2    Oshima, K.3
  • 61
    • 0000784961 scopus 로고
    • Noncatalyzed Stereoselective Allylation of Carbonyl Compounds with Allylsilacyclobutanes
    • Matsumoto, K.; Oshima, K.; Utimoto, K. Noncatalyzed Stereoselective Allylation of Carbonyl Compounds with Allylsilacyclobutanes. J. Org. Chem. 1994, 59, 7152-7155.
    • (1994) J. Org. Chem , vol.59 , pp. 7152-7155
    • Matsumoto, K.1    Oshima, K.2    Utimoto, K.3
  • 62
    • 33745775152 scopus 로고
    • Silicon-Directed Aldol Reactions. Rate Acceleration by Small Rings
    • Myers, A. G.; Kephart, S. E.; Chen, H. Silicon-Directed Aldol Reactions. Rate Acceleration by Small Rings. J. Am. Chem. Soc. 1992, 114, 7922-7923.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 7922-7923
    • Myers, A.G.1    Kephart, S.E.2    Chen, H.3
  • 63
    • 57749197179 scopus 로고    scopus 로고
    • Synthesis of Casuarine-Related Derivatives via 1,3-Dipolar Cycloaddition between a Cyclic Nitrone and an Unsaturated γ-Lactone
    • Stecko, S.; Solecka, J.; Chmielewski, M. Synthesis of Casuarine-Related Derivatives via 1,3-Dipolar Cycloaddition between a Cyclic Nitrone and an Unsaturated γ-Lactone. Carbohydr. Res. 2009, 344, 167-176.
    • (2009) Carbohydr. Res , vol.344 , pp. 167-176
    • Stecko, S.1    Solecka, J.2    Chmielewski, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.