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

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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 $NH_4OAc$.

A Practical Synthesis of Morita-Baylis-Hillman Adducts of Aryl Vinyl Ketones Catalyzed by a Proton Donor

  • Kim, Sung-Hwan;Kim, Se-Hee;Lim, Cheol-Hee;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.6
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    • pp.2023-2027
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    • 2012
  • An efficient and practical synthesis of MBH adducts of aryl vinyl ketones was developed using DABCO and 4-nitrophenol as a proton donor. Addition of a proton donor and the use of excess amounts (3.0 equiv) of aldehydes were highly beneficial for the yields of MBH adducts of aryl vinyl ketones.

Pd-Catalyzed Oxidative Arylation of Cinnamylphosphonates: An Efficient Synthesis of (Z)-Alkenylphosphonates

  • Lee, Hyun Seung;Lim, Cheol Hee;Lee, Hyun Ju;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3817-3822
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    • 2012
  • Various alkenylphosphonates were prepared via the palladium-catalyzed oxidative arylation of cinnamylphosphonates with arenes. The regioselectivity during the ${\beta}$-H elimination of the corresponding alkylpalladium intermediate was governed most likely by steric factors.

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.