• Title/Summary/Keyword: Morita-Baylis-Hillman reaction

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An Efficient Synthesis of Phospha-Morita-Baylis-Hillman Adducts via Michaelis-Arbuzov Reaction of the DABCO Salt of Morita-Baylis-Hillman Bromide

  • Kim, Sung Hwan;Kim, Se Hee;Lee, Hyun Seung;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.34 no.1
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    • pp.133-138
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    • 2013
  • An efficient synthesis of phospha-Morita-Baylis-Hillman adducts was carried out in good yields via the Michaelis-Arbuzov reaction of the DABCO salts of MBH bromides. Instead of a DABCO salt, a phosphonium salt could be effectively used for some substrates which showed some problems in the presence of DABCO.

Synthesis of Arene-Fused Isoindoline Derivatives from Morita-Baylis-Hillman Adducts by IMDA Reaction Using Z-Vinylarenes as 1,3-Dienes

  • Kim, Ko Hoon;Lim, Jin Woo;Moon, Hye Ran;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.35 no.11
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    • pp.3254-3260
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    • 2014
  • Intramolecular Diels-Alder (IMDA) reaction of vinylarenes bearing a Z-alkenyl tether, prepared from Morita-Baylis-Hillman (MBH) adducts, afforded arene-fused isoindoline derivatives in good yields. Vinylfurans, vinylthiophenes, and vinylnaphthalenes could be used successfully as dienes, while vinylbenzene failed under the same reaction conditions.

Morita-Baylis-Hillman Route to Dimethyl 2,3-Dihydrobenzo[b]oxepine-2,4-dicarboxylates and Methyl 2-(2-Carbomethoxybenzo[b]furan-3-yl)propanoates from Salicylaldehydes

  • Ahn, Sang-Hyun;Jang, Seung-Soon;Kim, Young-Keun;Lee, Kee-Jung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.1
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    • pp.233-242
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    • 2012
  • A new synthetic method for dimethyl 2,3-dihydrobenzo[b]oxepine-2,4-dicarboxylates and methyl 2-(2-carbomethoxybenzo[b]furan-3-yl)propanoates by an intramolecular conjugate displacement reaction or an $S_N2$ reaction of acetates of Morita-Baylis-Hillman adducts of methyl (2-formylphenoxy)acetates has been described.

Regioselective Synthesis of 1,3,4,5-Tetrasubstituted Pyrazoles from α-Alkenyl-α,β-Enones Derived from Morita-Baylis-Hillman Adducts

  • Kim, Sung Hwan;Lim, Jin Woo;Yu, Jin;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.2915-2920
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    • 2013
  • Convenient synthetic method for 4-arylethylpyrazoles and 4-styrylpyrazoles was developed using ${\alpha}$-alkenyl-${\alpha},{\beta}$-enones readily accessed from the Morita-Baylis-Hillman reaction. For the synthesis of 4-arylethylpyrazole, the reactions with arylhydrazines needed to be carried out in o-dichlorobenzene under $N_2$ balloon atmosphere. On the other hand, 4-styrylpyrazoles required the reactions in ethanol under $O_2$ balloon atmosphere.

An Efficient Synthesis of Poly-Substituted Phenols and Pyridines from Morita-Baylis-Hillman Acetates and Diethyl Oxalacetate

  • Yu, Jin;Kim, Ko Hoon;Lee, Hyun Ju;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.3027-3032
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    • 2013
  • Various phenol derivatives were synthesized in a one-pot reaction from MBH acetates and sodium diethyl oxalacetate via a [4C+2C] cyclization protocol. In addition, some pyridine derivatives could also be synthesized using the same starting materials, by isolating the $S_N2^{\prime}$ reaction intermediate and performing the cyclization with $NH_4OAc$.

Theoretical Mechanism Studies on the Enantioselectivity of aza-MBH-type Reaction of Nitroalkene to N-tosylimine Catalyzed by Thiourea-tertiary Amine

  • Lu, Nan;Wang, Huatian;Wang, Yangping
    • Bulletin of the Korean Chemical Society
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    • v.34 no.12
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    • pp.3591-3596
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    • 2013
  • The enantioselective aza-Morita Baylis Hillman reaction of nitroalkene and N-tosylimine catalyzed by thiourea-tertiary amine has been investigated using density functional theory. Enantioselectivity is dominated by the cooperative effect of non-covalent and weak covalent interactions imposed by different units of catalyst. As Lewis base, the tertiary amine unit activates nitroalkene via weak covalent bond. The weak covalent interaction orients the reaction in a major path with smaller variations of this bond. The aromatic ring unit activates N-tosylimine via ${\pi}-{\pi}$ stacking. The non-covalent interaction selects the major path with smaller changes of the efficient packing areas. Thiourea unit donates more compact H-bonded network for species of the major path. The calculated ee value in xylene solution phase (97.6%) is much higher than that in N,N-Dimethylformamide (27.2%). Our conclusion is also supported by NBO analysis.