19550-89-1Relevant academic research and scientific papers
Allylation of Aldehydes with Allyltin Compounds in Acidic Aqueous Media-A Catalytic Version
Yanagisawa, Akira,Morodome, Miwa,Nakashima, Hiroshi,Yamamoto, Hisashi
, p. 1309 - 1311 (1997)
Allylation reaction of aldehydes with allyltributyltin was achieved using Sn catalysts in acidic aqueous media. Exclusive aldehyde selectivity was observed for competitive reactions of aldehydes and ketones with allyltributyltin in the presence of 5 mol%
Preparation of homoallylic alcohols by reaction of aldehydes with η3-allyl- and η3-crotylmolybdenum complexes
Gable,Shanmugham,White
, p. 704 - 707 (2000)
η3-Allyl and η3-methallyl complexes of molybdenum react with aldehydes to give homoallylic alcohols in preparative yields when water is used as a proton source, but the scope of the reaction is narrowed in the case of the η3-crotylmolybdenum complex by the formation of both transposed and nontransposed products.
Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates
Park, Yunjeong,Lee, Ji Sun,Ryu, Jae-Sang
supporting information, p. 2183 - 2188 (2021/03/15)
An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).
Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination
Kakiuchi, Fumitoshi,Kochi, Takuya,Kumagai, Takaaki,Muto, Kazuma
supporting information, p. 24500 - 24504 (2021/10/19)
Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.
Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl3
López-Martínez, Josefa L.,Torres-García, Irene,Rodríguez-García, Ignacio,Mu?oz-Dorado, Manuel,álvarez-Corral, Miriam
, p. 806 - 816 (2019/01/24)
CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis of natural products.
Method for synthesizing 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring
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Paragraph 0018-0023; 0026, (2019/10/01)
The invention discloses a method for synthesizing 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring. The synthesis method includes the following steps: performing Grignard reaction on an aldehyde or ketone to obtain an allyl alcohol compound; and performing condensation reaction with 2-(tert-butylsulfonyl)acetic acid to obtain an allyl (tert-butylsulfonyl)acetate compound; performing olefin cross-metathesis reaction under the action of a second generation Grubbs catalyst to obtain a methoxycarbonyl (tert-butylsulfonyl)acetate compound; performing intramolecular reaction byusing anhydrous N,N-dimethylformamide as a solvent in the presence of a catalyst palladium acetate and a ligand triphenylphosphine, so as to produce a 3-tert-butylsulfonyl 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring lactone compound; and finally removing tert-butylsulfonyl in a reaction solution of sodium amalgam and acetic acid by taking ethanol as a solvent, so as toobtain 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring lactone compound. The yield of the method is high, and a solution with a very dilute reaction concentration is not neededin the synthesis of various substituted octatomic ring lactones through intramolecular catalysis by palladium, so the process conditions are simple and universal.
Syntheses of 4-Acetoxy-or acetylthio-2-substituted tetrahydrothiophene
Li, Yaxi,Ding, Rui,Liu, Yongguo,Ma, Bianbian,Sun, Baoguo,Tian, Hongyu
, p. 254 - 272 (2018/02/22)
The generality of a three-step route for the preparation of 4-Acetoxy-2-Alkyltetrahydrothiophenes was investigated, which started from 1-Alken-4-ols including epoxidation, mesylation and intramolecular nucleophilic substitution. 4-Acetoxy-2-Alkyltetrahydr
Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction
Denmark, Scott E.,Matesich, Zachery D.,Nguyen, Son T.,Milicevic Sephton, Selena
, p. 23 - 48 (2018/02/19)
The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon-carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.
Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
supporting information, p. 2056 - 2059 (2017/02/15)
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
Remarkable Influence of Cobalt Catalysis on Epoxide Ring-Opening with Sulfoxonium Ylides
Jamieson, Megan L.,Brant, Nicola Z.,Brimble, Margaret A.,Furkert, Daniel P.
, p. 3952 - 3956 (2017/08/29)
Cobalt demonstrates a remarkable ability to catalytically divert the course of epoxide to oxetane ring expansion via reaction with a sulfoxonium ylide. An expanded survey of transition-metal catalysts has confirmed that cobalt salts uniquely instead deliv
