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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 6
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Original Articles

Silyl Ketene Acetal Chemistry: Steric Limitations in Lewis Acid-Promoted Addition of Ketones

Wenke G. Department of Chemistry, New York University, New York, New York, 10003
,
Jacobsen E. N. Department of Chemistry, New York University, New York, New York, 10003
,
Totten G. E. Department of Chemistry, New York University, New York, New York, 10003
,
Karydas A. C. Department of Chemistry, New York University, New York, New York, 10003
&
Rhodes Y. E. Department of Chemistry, New York University, New York, New York, 10003
Pages 449-458 | Published online: 03 Jan 2007

Citations (18)

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Read on this site (2)

Rudhramyna Gnaneshwar & Swaminathan Sivaram. (2010) Addition of a Silyl Ketene Acetal to α,β-Unsaturated Cyclic Anhydrides. Synthetic Communications 40:16, pages 2353-2363.
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G.E. Totten, G. Wenke & Y.E. Rhodes. (1985) Dimerization of Silyl Ketene Acetal: Effect of Lewis Acid Selection on Product Yield and Structure. Synthetic Communications 15:4, pages 291-300.
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Articles from other publishers (16)

Majid M. Heravi & Vahideh Zadsirjan. 2021. Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids. Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids 295 323 .
Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 139 .
Mina C. Nakhla & John L. Wood. (2017) Total Synthesis of (±)-Aspergilline A. Journal of the American Chemical Society 139:51, pages 18504-18507.
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Hikaru Yanai, Yasuhiro Yoshino, Arata Takahashi & Takeo Taguchi. (2010) Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones. The Journal of Organic Chemistry 75:15, pages 5375-5378.
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Ryohei Nagase, Jun Osada, Hiroaki Tamagaki & Yoo Tanabe. (2010) Pentafluorophenylammonium Trifluoromethanesulfonimide: Mild, Powerful, and Robust Catalyst for Mukaiyama Aldol and Mannich Reactions between Ketene Silyl Acetals and Ketones or Oxime Ethers. Advanced Synthesis & Catalysis 352:7, pages 1128-1134.
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De Lie An, Zhihong Peng, Akihiro Orita, Akinobu Kurita, Sumiyo Man‐e, Kei Ohkubo, Xingshu Li, Shunichi Fukuzumi & Junzo Otera. (2006) Organotin Perfluorooctanesulfonates as Air‐Stable Lewis Acid Catalysts: Synthesis, Characterization, and Catalysis. Chemistry – A European Journal 12:6, pages 1642-1647.
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Isamu Matsuda. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
René Csuk & Martina Schaade. (1994) Fluoride mediated reactions of lactones with silyl ketene acetals. Tetrahedron 50:11, pages 3333-3348.
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René Csuk, Martina Schaade & Andrea Schmidt. (1994) Diastereoselective dimerization of aldonolactones. Tetrahedron 50:41, pages 11885-11892.
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René Csuk & Martina Schaade. (1993) Convenient fluoride-mediated reactions of lactones with silyl ketene acetals. Tetrahedron Letters 34:49, pages 7907-7910.
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Boris A Cheskis, Natalya M Ivanova, Aiexsander M Moiseenkov & Oleg M Nefedov. (1993) The chemistry of acetylcyclopropane. Russian Chemical Reviews 62:4, pages 337-358.
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Daniel Belluš & Beat Ernst. (2003) Cyclobutanones and Cyclobutenones in Nature and in Synthesis [New Synthetic Methods(71)]. Angewandte Chemie International Edition in English 27:6, pages 797-827.
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Daniel Belluš & Beat Ernst. (2006) Cyclobutanone und Cyclobutenone in der Natur und in der Synthese. Angewandte Chemie 100:6, pages 820-850.
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M. Bellassoued, R. Ennigrou & M. Gaudemar. (1988) Bis(triméthylsiloxy)-1,1 butadiène-1,3 et triméthylsilyl-4 butène-2 oate de triméthylsilyle: préparations et réactions avec le benzaldéhyde. Journal of Organometallic Chemistry 338:2, pages 149-158.
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Yasuyuki Kita, Hitoshi Yasuda, Osamu Tamura, Fumio Itoh, Yuan Ke Ya & Yasumitsu Tamura. (1985) The chemistry of O-silylated ketene acetals; diastereoselective Aldol reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes leading to 2-deoxy-D (and L)-riboses. Tetrahedron Letters 26:47, pages 5777-5780.
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G. WENKE, E. N. JACOBSEN, G. E. TOTTEN, A. C. KARYDAS & Y. E. RHODES. (2016) ChemInform Abstract: SILYL KETENE ACETAL CHEMISTRY: STERIC LIMITATIONS IN LEWIS ACID‐PROMOTED ADDITION OF KETONES. Chemischer Informationsdienst 14:42.
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