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

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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.

Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts

  • Lim, Cheol-Hee;Kim, Sung-Hwan;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1622-1626
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    • 2012
  • An efficient synthetic method of various 5-hydroxy-3-pyrrolin-2-one derivatives has been developed starting from the MBH adducts. In addition, some synthetic applicability of the prepared 5-hydroxy-3-pyrrolin-2-ones was demonstrated including the synthesis of lactam-fused tetrahydroisoquinolines.

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.

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.