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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 1
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Original Articles

Trimethylsilylmethyl Ketones in Synthesis A Regiospecific Synthesis of β, γ-Unsaturated Esters, Amides and Nitriles

R. A. Ruden Department of Chemistry, Rutgers The State University, New Brunswick, New Jersey, 08903
&
B. L. Gaffney Department of Chemistry, Rutgers The State University, New Brunswick, New Jersey, 08903
Pages 15-19 | Received 13 Sep 1974, Published online: 05 Dec 2006

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M.B. Anderson & P.L. Fuchs. (1987) An Efficient Method for Conversion of Carboxylic Acid Derivatives to Allylsilanes1 . Synthetic Communications 17:6, pages 621-635.
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Articles from other publishers (34)

Ana M. González-Nogal & Purificación Cuadrado. (2013) Epoxysilanes as substrates in regio- and stereo-specific synthesis of silylated γ-hydroxyphosphane oxides, precursors of stereodefined allylphosphane oxides. Tetrahedron 69:37, pages 8080-8087.
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D. Patrick Green & Dmitry Zuev. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Louis F. Fieser, Mary Fieser & Tse-Lok HoTse-Lok Ho, Mary Fieser & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser & William Roush. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
David J. Ager & David Ager. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Tony C. T. Chang, Myron Rosenblum & Nancy Simms. 2003. Organic Syntheses. Organic Syntheses 95 95 .
David J. Ager. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Gerald L. Larson. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Larry C. Blaszczak. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
D. Patrick Green. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Narayan G Bhat, Chris Martinez & J De Los Santos. (2000) A novel synthesis of β-ketosilanes via organoboranes. Tetrahedron Letters 41:34, pages 6541-6544.
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Hidenori Watanabe, Takahiro Onoda, Takeshi Kitahara & Kenji Mori. (1997) Synthesis of (+)-sorokinianin. Tetrahedron Letters 38:34, pages 6015-6018.
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Stephen Hanessian, Teresa Abad-Grillo & Grant McNaughton-Smith. (1997) Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)-butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron. Tetrahedron 53:18, pages 6281-6294.
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Dieter Enders, Braj B. Lohray, Frank Burkamp, Vidya Bhushan & Robert Hett. (2006) Regio‐ and Enantioselective Synthesis of α‐Silyl Aldehydes and Ketones via SAMP/RAMP Hydrazones. Liebigs Annalen 1996:2, pages 189-200.
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. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1147 1316 .
Anita R. Maguire. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 589 671 .
David J. Ager. 2004. Organic Reactions. Organic Reactions 1 223 .
Susumu Sato, Isamu Matsuda & Yusuke Izumi. (1988) A regiodefined synthesis of α-trimethylsilyl ketones catalyzed by rhodium(I) hydride complex. Journal of Organometallic Chemistry 344:1, pages 71-88.
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Dieter Enders & Braj Bhushan Lohary. (1987) Enantioselektive Synthese von α-Trialkylsilylketonen und -aldehyden. Angewandte Chemie 99:4, pages 359-360.
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B.A. Narayanan & W.H. Bunnelle. (1987) The cerium mediated conversion of esters to allylsilanes. Tetrahedron Letters 28:50, pages 6261-6264.
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Isamu Matsuda & Susumu Sato. (1986) Regiodefined synthesis of α-bromo, α-phenylthio, and α-phenylseleno ketones by means of specific substitution of the trimethylsilyl group in α-trimethylsilyl ketones. Journal of Organometallic Chemistry 314:1-2, pages 47-52.
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Susumu Sato, Isamu Matsuda & Yusuke Izumi. (1985) An oxidative route to α-trimethylsilyl ketones by means of rhodium catalyzed dehydrogenation of β-trimethylsilyl alcohols. Tetrahedron Letters 26:35, pages 4229-4230.
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Gerald L Larson, Ingrid Montes de López-Cepero & Luz E Torres. (1984) An efficient synthesis of β-ketosilanes. Tetrahedron Letters 25:16, pages 1673-1676.
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Susumu Sato, Hisashi Okada, Isamu Matsuda & Yusuke Izumi. (1984) A versatile route to silylsubstituted ketones by rhodium catalyzed isomerization of silylated allyl alcohols. Tetrahedron Letters 25:7, pages 769-770.
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Susumu Sato, Isamu Matsuda & Yusuke Izumi. (1983) A facile synthesis of α-trimethylsilyl ketones and their regiospecific rearrangement to trimethylsilyl enol ethers. Tetrahedron Letters 24:36, pages 3855-3858.
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Tapio A. Hase & Leila Lahtinen. (1982) Silicon migration and ring cleavage reactions of 2-alkyl-2-trimethylsilylmethyl-1,3-dithianes. Journal of Organometallic Chemistry 240:1, pages 9-16.
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P.D. Magnus, T. Sarkar & S. Djuric. 1982. Comprehensive Organometallic Chemistry. Comprehensive Organometallic Chemistry 515 659 .
D.A. Armitage. 1982. Comprehensive Organometallic Chemistry. Comprehensive Organometallic Chemistry 1 203 .
Ernest W. Colvin. 1981. Silicon in Organic Synthesis. Silicon in Organic Synthesis 141 164 .
Michio Obayashi, Kiitiro Utimoto & Hitosi Nozaki. (1979) A Highly Stereoselective Synthesis of Trisubstituted Ethylenes from α-Trialkylsilyl Ketones. Bulletin of the Chemical Society of Japan 52:6, pages 1760-1764.
Crossref
Martin Demuth. (2004) Efficient Conversion of Esters to α‐Trimethylsilylketones. Preliminary communication. Helvetica Chimica Acta 61:8, pages 3136-3138.
Crossref
. 1978. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 305 335 .
Paul F. Hudrlik, R.N. Misra, G.P. Withers, A.M. Hudrlik, R.J. Rona & J.P. Arcoleo. (1976) Magnesium bromide induced rearrangements of α,β-epoxysilanes. Tetrahedron Letters 17:18, pages 1453-1456.
Crossref
R. A. RUDEN & B. L. GAFFNEY. (2016) ChemInform Abstract: TRIMETHYLSILYLMETHYL KETONES IN SYNTHESIS. A REGIOSPECIFIC SYNTHESIS OF BETA,GAMMA‐UNSATURATED ESTERS, AMIDES AND NITRILES. Chemischer Informationsdienst 6:29.
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