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Stereochemical Studies on the Addition of Allylsilanes to Aldehydes. The SE' Component

Cite this: J. Org. Chem. 1994, 59, 18, 5130–5132
Publication Date (Print):September 1, 1994
https://doi.org/10.1021/jo00097a008
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    3. Jinping Yuan, Pankaj Jain, Jon C. Antilla. Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes. The Journal of Organic Chemistry 2020, 85 (20) , 12988-13003. https://doi.org/10.1021/acs.joc.0c01646
    4. Shou-Jie Shen and Wei-Dong Z. Li . Formal Homoiodo Allylsilane Annulations: Dual Total Syntheses of (±)-Hirsutene and (±)-Capnellene. The Journal of Organic Chemistry 2013, 78 (14) , 7112-7120. https://doi.org/10.1021/jo4009854
    5. Larry M. Wolf and Scott E. Denmark . A Theoretical Investigation on the Mechanism and Stereochemical Course of the Addition of (E)-2-Butenyltrimethylsilane to Acetaldehyde by Electrophilic and Nucleophilic Activation. Journal of the American Chemical Society 2013, 135 (12) , 4743-4756. https://doi.org/10.1021/ja311889v
    6. Linjie Li, Xincui Ye, Ya Wu, Lu Gao, Zhenlei Song, Zhiping Yin, and Yongjin Xu . Sakurai Reaction of 3,3-Bis(silyl) Silyl Enol Ethers with Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid. Organic Letters 2013, 15 (5) , 1068-1071. https://doi.org/10.1021/ol400069p
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    14. Pavel Kočovský,, Ghafoor Ahmed,, Jiří Šrogl,, Andrei V. Malkov, and, John Steele. New Lewis-Acidic Molybdenum(II) and Tungsten(II) Catalysts for Intramolecular Carbonyl Ene and Prins Reactions. Reversal of the Stereoselectivity of Cyclization of Citronellal. The Journal of Organic Chemistry 1999, 64 (8) , 2765-2775. https://doi.org/10.1021/jo9821675
    15. Andrea Bottoni,, Anna Luisa Costa,, Donata Di Tommaso,, Ivan Rossi, and, Emilio Tagliavini. New Computational and Experimental Evidence for the Mechanism of the Sakurai Reaction. Journal of the American Chemical Society 1997, 119 (50) , 12131-12135. https://doi.org/10.1021/ja9723693
    16. Ian Fleming,, Asuncion Barbero, and, David Walter. Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds. Chemical Reviews 1997, 97 (6) , 2063-2192. https://doi.org/10.1021/cr941074u
    17. Hsin-Guo Shu,, Lin-Hung Shiu,, Shin-Hwan Wang,, Sue-Lein Wang,, Gene-Hsian Lee,, Shie-Ming Peng, and, Rai-Shung Liu. Tungsten η1-Five-Membered Oxygenated Heterocycles Derived from Tungsten η1-Propargyl Compounds:  Systematic Syntheses, Structural Rearrangement, Electrophilic Alkylations, and Oxidative Demetalations. Journal of the American Chemical Society 1996, 118 (3) , 530-540. https://doi.org/10.1021/ja9518888
    18. Ksenia S. Stankevich, Matthew J. Cook. The Hosomi-Sakurai allylation in carbocyclization reactions. Tetrahedron Letters 2023, 121 , 154415. https://doi.org/10.1016/j.tetlet.2023.154415
    19. Richard C. Larock, Cristiano Raminelli. Formation of Alcohols and Phenols by Alkylation of Carbonyl Compounds. 2018, 1-97. https://doi.org/10.1002/9781118662083.cot07-009
    20. Jiping Fu, Shinji Fujimori, Scott E. Denmark. Bifunctional Lewis Base Catalysis with Dual Activation of X 3 Si – Nu and C = O ( n → σ * ). 2016, 281-338. https://doi.org/10.1002/9783527675142.ch9
    21. Eugenia Marqués‐López, Raquel P. Herrera. Essential Multicomponent Reactions I. 2015, 382-415. https://doi.org/10.1002/9781118863992.ch12
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    23. Tamejiro Hiyama. Organosilicon and Relating Organotin Chemistry. 2013, 373-544. https://doi.org/10.1002/9781118484722.ch3
    24. Michael A. Brook, Mustafa Mohamed. Lewis Acid‐Mediated Addition of Amino Acid‐Substituted α ‐Allylsilanes to Aromatic Acetals. Helvetica Chimica Acta 2012, 95 (12) , 2660-2671. https://doi.org/10.1002/hlca.201200533
    25. Scott E. Denmark, Eric J. Weber, Neil G. Almstead, Larry M. Wolf. On the stereochemical course of the addition of allylsilanes to aldehydes. Tetrahedron 2012, 68 (37) , 7701-7718. https://doi.org/10.1016/j.tet.2012.05.084
    26. Paul F. Hudrlik, Anne M. Hudrlik, Yassin A. Jeilani. Intramolecular nucleophilic attack at silicon in o-silylbenzyl alcohols. Generation of allyl and benzyl anion equivalents. Tetrahedron 2011, 67 (52) , 10089-10096. https://doi.org/10.1016/j.tet.2011.09.127
    27. Wen‐Tau T. Chang, Russell C. Smith, Christopher S. Regens, Aaron D. Bailey, Nathan S. Werner, Scott E. Denmark. Cross‐Coupling with Organosilicon Compounds. 2011, 213-746. https://doi.org/10.1002/0471264180.or075.03
    28. Kazunori Takahashi, Kentaro Takeda, Toshio Honda. Efficient formal synthesis of (±)-axamide-1 and (±)-axisonitrile-1 via an intramolecular Hosomi–Sakurai reaction. Tetrahedron Letters 2010, 51 (27) , 3542-3544. https://doi.org/10.1016/j.tetlet.2010.04.119
    29. Tien‐Yau Luh, Shiuh‐Tzung Liu. Synthetic Applications of Allylsilanes and Vinylsilanes. 2009https://doi.org/10.1002/9780470682531.pat0192
    30. James R. Green, Babajide I. Alo, Marek Majewski, Victor Snieckus. γ-Silylated α,β-unsaturated amides — Preparation by [1,5]-sigmatropic rearrangement and use as masked dienolate equivalents in carbonyl condensations. Canadian Journal of Chemistry 2009, 87 (6) , 745-759. https://doi.org/10.1139/V09-054
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    33. Scott E. Denmark, Gregory L. Beutner. Lewis‐Base‐Katalyse in der organischen Synthese. Angewandte Chemie 2008, 120 (9) , 1584-1663. https://doi.org/10.1002/ange.200604943
    34. Scott E. Denmark, Gregory L. Beutner. Lewis Base Catalysis in Organic Synthesis. Angewandte Chemie International Edition 2008, 47 (9) , 1560-1638. https://doi.org/10.1002/anie.200604943
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    37. Yu‐hong Lam, Carla Bobbio, Ian R. Cooper, Véronique Gouverneur. A Concise Synthesis of Enantioenriched Fluorinated Carbocycles. Angewandte Chemie 2007, 119 (27) , 5198-5202. https://doi.org/10.1002/ange.200701365
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    40. Vanda Cerè, Antonella Capperucci, Alessandro Degl’Innocenti, Salvatore Pollicino. Stereoconservative protodesilylation of substituted silyl dithianes. Tetrahedron Letters 2006, 47 (43) , 7525-7528. https://doi.org/10.1016/j.tetlet.2006.08.078
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    43. Andrei V. Malkov, Lenka Dufková, Louis Farrugia, Pavel Kočovský. Quinox, a Quinoline‐Type N ‐Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions. Angewandte Chemie 2003, 115 (31) , 3802-3805. https://doi.org/10.1002/ange.200351737
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    49. Chiaki Kuroda, Atsushi Murase, Hideyuki Suzuki, Toru Endo, Shuzo Anzai. Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yl]cyclohexanecarbaldehyde with Loss of Formyl Carbon. Bulletin of the Chemical Society of Japan 1998, 71 (7) , 1639-1647. https://doi.org/10.1246/bcsj.71.1639
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