105875-75-0Relevant academic research and scientific papers
Divergent Functionalization of Indoles with Acryloyl Silanes via Rhodium-Catalyzed C-H Activation
Lu, Ping,Feng, Chao,Loh, Teck-Peng
, p. 3210 - 3213 (2015)
(Chemical Equation Presented) A protocol enabled by rhodium-catalyzed C-H functionalization of indoles with acryloyl silanes was developed, providing a convenient and highly effective method for the synthesis of functionalized acylsilane derivatives. By tuning the reaction condition, this C-H-activation-initiated reaction proceeds divergently with acryloyl silianes to selectively afford alkylation or alkenylation products via hydroarylation or oxidative cross-coupling, respectively. The mild reaction conditions employed in both cases enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. Furthermore, polycyclic indole derivatives were easily accessed from 2-alkenylation products through a visible-light-induced reaction cascade.
α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita–Baylis–Hillman Reactions
Marri, Gangababu,Justaud, Frédéric,Das, Saibal,Grée, René
, p. 56 - 65 (2018/11/30)
α-β-unsaturated acylsilanes are excellent substrates for Morita–Baylis–Hillman (MBH) reactions, affording the expected adducts in good to excellent yields. In these derivatives, as well as the corresponding acetates, the acylsilanes can be smoothly transf
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
supporting information, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Synthesis of acylsilanes via nickel-catalyzed reactions of α-hydroxyallylsilanes
Reddy, Gangireddy PavanKumar,Reddy, J. Satyanarayana,Das, Saibal,Roisnel, Thierry,Yadav, Jhillu S.,Chandrasekhar, Srivari,Gree, Rene
supporting information, p. 1524 - 1527 (2013/06/27)
The redox isomerization processes and tandem isomerization-aldolization reactions, mediated by nickel catalysts, offer new versatile entries to acylsilanes. For the second reaction, high diastereoselectivities, up to 98:2, have been obtained with bulky substituents on silicon.
Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes
Higashino, Masato,Ikeda, Naoko,Shinada, Tetsuro,Sakaguchi, Kazuhiko,Ohfune, Yasufumi
supporting information; experimental part, p. 422 - 425 (2011/03/21)
A novel silyl group-directed anti-SN2′ reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of α-hydroxy-α-alkenylsilanes with a TBS or TIPS group gave the anti-SN2′ product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group.
Enzymatic kinetic resolution of α-hydroxysilanes
An, Ilhwan,Onyeozili, Edith N.,Maleczka Jr., Robert E.
experimental part, p. 527 - 534 (2010/08/22)
The enzymatic kinetic resolution of α-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various α-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active α-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees.
Enantioselective reduction of α,β-unsaturated acylsilanes by chiral lithium amides
Takeda, Kei,Ohnishi, Yuji,Koizumi, Toru
, p. 237 - 239 (2008/02/12)
(equation presented) Reaction of β-substituted acryloylsilanes I with lithium amides II affords α-silyl allylic alcohols III in high enantiomeric excess (>99percent) via formal hydride transfer from the chiral lithium amide.
Syntheses of Cyclopropyl Silyl Ketones
Scheller, Markus E.,Frei, Bruno
, p. 44 - 53 (2007/10/02)
The synthesis of the cyclopropyl silyl ketones 1-4 is described.The trimethylsilyl ketone 1 was prepared from geraniol ((E)-5) in ca. 10percent overall yield by cyclopropanation leading to 6, CrO3 oxidation to the aldehyde 8, reaction of the latter with trimethylsilyl anion to 14A+B, and CrO3 oxidation to 1.Also for the (t-butyl)dimethylsilyl ketones 2-4, an efficient four-step synthesis with overall yields of 48percent, 85percent, and 13percent, respectively, was elaborated, starting from the allylic alcohols (E)-5, (Z)-5, and 23.The method for the preparation involves as the key step a Wittig rearrangement of the silylalyl ethers ((E/Z)-20, 24) to the silyl alcohols ((E/Z)-21, 25), subsequent cyclopropanation (19A+B, 22A+B, 26), and oxidation to the cyclopropyl silyl ketones 2-4.
