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Cas Database




  • Product Name:(R)-(Z)-1-hydroxy-1-phenyl-2-butene

  • CAS Number: 100017-30-9


  • Molecular Weight:148.205

  • Molecular Formula:C10H12O

  • HS Code:

  • Mol File:100017-30-9.mol


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    Relevant articles and documentsAll total 20 Articles be found

    Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

    Bedná?ová, Eva,Dra?ínsky, Martin,Malatinec, ?tefan,Císa?ová, Ivana,Lamaty, Frédéric,Kotora, Martin

    supporting information, p. 2869 - 2878 (2018/08/17)

    A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).

    Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

    Beltran, Frédéric,Bergamaschi, Enrico,Funes-Ardoiz, Ignacio,Teskey, Christopher J.

    supporting information, p. 21176 - 21182 (2020/09/17)

    Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

    H-*BEA Zeolite-Catalyzed Nucleophilic Substitution in Allyl Alcohols Using Sulfonamides, Amides, and Anilines

    Aoki, Shunsuke,Fujii, Takeshi,Morita, Sachiko,Nishida, Ryo,Ohtsuki, Akimichi,Okumura, Kazu

    , (2020/07/24)

    Herein, we report a novel zeolite-catalyzed nucleophilic substitution in allyl alcohols. The product yield was improved upon the addition of NaOTf (0.05 mol-percent) using the studied zeolites. The highest yields were observed using H-*BEA(Si/Al2 = 40)/NaOTf. The scope of the reaction with respect to the nucleophile was examined using 1,3-diphenylprop-2-ene-1-ol as a model substrate under optimized reaction conditions. p-Substituted aryl sulfonamides bearing electron-rich or electron-deficient substituents, alkyl sulfonamides, and heteroaryl sulfonamides undergo the amidation reaction to produce their corresponding allyl sulfonamides in good yield. Amides and anilines exhibited low activity under the optimized conditions, however, performing the reaction at 90 °C produced the target product. The scope of the allyl alcohol was investigated using p-toluenesulfonamide as the nucleophile and the reaction proceeded with a variety of allylic alcohols. To probe the practical utility of the H-*BEA-catalyzed amidation reaction, a gram-scale reaction was performed using 1.01 g (4.8 mmol) of allyl alcohol, which afforded the target product in 88 percent yield.

    Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

    Lu, Fu-Dong,Lu, Liang-Qiu,He, Gui-Feng,Bai, Jun-Chuan,Xiao, Wen-Jing

    supporting information, p. 4168 - 4173 (2021/04/06)

    1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.

    Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

    Goncalves-Contal, Sylvie,Gremaud, Ludovic,Palais, La?titia,Babel, Lucille,Alexakis, Alexandre

    , p. 3301 - 3308 (2016/09/12)

    β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

    Process route upstream and downstream products

    Process route

    With hydrido(phosphonite)cobalt(I); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane;Inbenzene;at 20 ℃; for 16h; Overall yield = 71 percent; Overall yield = 21 mg; Sealed tube; Inert atmosphere; Irradiation; Schlenk technique;
    Multi-step reaction with 2 steps
    1.1: aluminum (III) chloride / dichloromethane / 0.33 h / 20 °C / Schlenk technique; Inert atmosphere
    1.2: 4 h / 20 °C / Schlenk technique; Inert atmosphere
    2.1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; hydrido(phosphonite)cobalt(I) / benzene / 16 h / 20 °C / Sealed tube; Inert atmosphere; Irradiation; Schlenk technique
    With aluminum (III) chloride; hydrido(phosphonite)cobalt(I); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane;Indichloromethane; benzene;
    cis-2-phenyl-3-ethenyl oxirane

    cis-2-phenyl-3-ethenyl oxirane



    With Schwartz's reagent; sodium hydrogencarbonate;Indichloromethane;Ambient temperature;
    With zirconocene hydrochloride;Indichloromethane;at 20 ℃;
    Multistep reaction; (i) tBuLi, THF, ether, pentane, (ii) /BRN= 471223/, (iii) aq. AcOH;
    phenylmagnesium bromide; crotonaldehyde;With chloro-trimethyl-silane; copper(I) thiophene-2-carboxylate; (R)-tol-BINAP;Indiethyl ether;at -78 ℃; Inert atmosphere;
    With hydrogenchloride;Inmethanol; diethyl ether; water;optical yield given as %ee; enantiospecific reaction; Inert atmosphere;
    phenylmagnesium bromide;With copper(I) thiophene-2-carboxylate; (R)-tol-BINAP;Indiethyl ether;at -78 ℃; for 0.25h; Inert atmosphere;
    crotonaldehyde;With chloro-trimethyl-silane;Indiethyl ether;at -78 ℃; for 8h; enantioselective reaction; Inert atmosphere;
    48 % ee
    Intetrahydrofuran; diethyl ether;at 0 - 20 ℃; for 7.5h;
    Intetrahydrofuran; diethyl ether;at 0 - 20 ℃; for 1h; Inert atmosphere;
    Intetrahydrofuran;at 0 - 20 ℃;
    bromobenzene;With iodine; magnesium;Intetrahydrofuran;at 20 ℃; for 1.5h;
    crotonaldehyde;Intetrahydrofuran;at 0 - 20 ℃; for 2h;
    bromobenzene;With magnesium;Intetrahydrofuran;
    crotonaldehyde;Intetrahydrofuran;at 0 ℃;
    With water;Intetrahydrofuran;
    With triethyl borane; triphenylphosphine; palladium diacetate;Intetrahydrofuran; hexane;at 25 ℃; for 35h;
    With sodium tetrahydroborate; calcium chloride;Inmethanol;1a) 30 min, 25 deg C, 1b) 0 deg C, 1 h;
    With potassium tert-butylate;Inisopropyl alcohol;at 90 ℃; for 0.533333h; Flow reactor; Inert atmosphere;
    With sec.-butyllithium;Intetrahydrofuran;at -78 ℃; for 2h;

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