• Title/Summary/Keyword: ${\alpha},{\beta}-unsaturated\

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Organocatalytic Enantioselective Michael Addition of α-Nitroacetate to α,β-Unsaturated Enones: A Route to Chiral γ-Nitro Ketones and δ-Keto Esters

  • Moon, Hyoung-Wook;Kim, Dae-Young
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.291-295
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    • 2011
  • The catalytic enantioselective conjugate addition reaction of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones promoted by chiral bifunctional organocatalysts is described. The treatment of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones afforded the corresponding Michael adducts with high enantioselectivity. The conjugate addition adducts are easily converted to chiral $\gamma$-nitro ketones and $\delta$-keto esters.

Reductive Amination of ${\alpha}$,${\beta}$-Unsaturated Carbonyl Compounds with Tetracarbonylhydridoferrate as a Reducing Agent (${\alpha}$,${\beta}$-不飽和 카르보닐化合物의 還元 아미노화反應)

  • Kim Hong-Seok;Shim Sang Chul;Shim Sang Chull
    • Journal of the Korean Chemical Society
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    • v.23 no.2
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    • pp.99-103
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    • 1979
  • The reductive amination of three ${\alpha}$,${\beta}$-unsaturated aldehydes, cinnamaldehyde, crotonaldehyde, and acrolein are carried out successfully by tetracarbonylhydridoferrate in the presence of various primary amines. In a typical reaction, a mixture of potassium tetracarbonylhydridoferrate (22 mmole), an amine (22∼44 mole) and ${\alpha}$,${\beta}$-unsaturated aldehyde (22 mmole), in ethanol (30∼50 ml) was stirred for 9∼60 hours at room temperature under carbon monoxide atmosphere. All the products were characterized as secondary amines by mass, infrared, and nmr spectra as well as gas chromatographic data.

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Selective Reduction of $\alpha,\beta$-Unsaturated Ketones with Borohydride Exchange Resin-$CuSO_4$ in Methanol

  • Yoon, Nung-Min;Sim, Tae-Bo
    • Bulletin of the Korean Chemical Society
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    • v.14 no.6
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    • pp.749-752
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    • 1993
  • Borohydride exchange resin $(BER)-CuSO_4$ system readily reduces {\alpha},{\beta}$-unsaturated ketones to the corresponding saturated alcohols quantitatively. This reduction tolerates many functional groups such as carbon-carbon multiple bonds, chlorides, epoxides, esters, amides and nitriles.

Concomitant Addition and Acetalization of α,β-Unsaturated Aldehydes with Diols

  • Jeon, Kyu-Ok;Yu, Ji-Sook;Lee, Chang-Kiu
    • Bulletin of the Korean Chemical Society
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    • v.25 no.11
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    • pp.1653-1656
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    • 2004
  • ${\alpha},{\beta}$-Unsaturated aldehydes such as acrolein and crotonaldehyde were reacted with diols in the presence of conc. sulfuric acid to give products of which concomitant addition to C-C double bond and acetalization took place. Boron trifluoride etherate and titanium tetrachloride gave only acetalization products.

Structural Studies by NMR (Ⅰ). Conformations and Configurations of ${\alpha},{\beta}$-Unsaturated Phenylhydrazones (NMR에 의한 입체구조에 관한 연구 (제1보). ${\alpha},{\beta}$-Unsaturated Phenylhydrazones의 Conformation과 Configuration에 대하여)

  • Lee Hak-ki;Lim Yong Jin;Choi Jung Do
    • Journal of the Korean Chemical Society
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    • v.18 no.3
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    • pp.215-220
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    • 1974
  • Conformations and cofigurations were studied for some ${\alpha},{\beta}$-unsaturated phenylhydrazones which have similar structures to the stucture of butenedial bistosylhydrazone, a precursor of tetrahedrane, by the analysis of their nmr spectra. The chemical shift difference between two solvents, benzene and aliphatic solvents, was applied for the assigning syn and anti structures of phenylhydrazone isomers as a convenient method. In this work, it was found that the phenylhydrazones have syn configurations and also found that the dihedral angles of $CH_a-CH_b$ are around $150^{\circ}$ at room temperature from the the interpretation of the vicinal spin-spin coupling constants. These results were discussed in concerning with their conformations.

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