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Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts
김재녕,이가영,Saravanan Gowrisankar 대한화학회 2005 Bulletin of the Korean Chemical Society Vol.26 No.10
Carbon-carbon single bond-forming reaction is the most useful and fundamental reaction in organic synthesis. Most of the basic carbon-carbon single bond-forming reactions, thus, developed in the past. In these respects, conceptually new C-C bond formation reaction can be highlighted. The Baylis-Hillman reaction was found at the early 1970’s. However, extensive studies on this highly potential reaction were started only before 15 years. This review has been written to shed more lights to the importance of Baylis-Hillman reaction. We have focused mainly on the reaction mechanism, conceptually related reactions, and chemical transformations of the Baylis-Hillman adducts.
Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts
Lee, Ka-Young,Gowrisankar, Saravanan,Kim, Jae-Nyoung Korean Chemical Society 2005 Bulletin of the Korean Chemical Society Vol.26 No.10
Carbon-carbon single bond-forming reaction is the most useful and fundamental reaction in organic synthesis. Most of the basic carbon-carbon single bond-forming reactions, thus, developed in the past. In these respects, conceptually new C-C bond formation reaction can be highlighted. The Baylis-Hillman reaction was found at the early 1970’s. However, extensive studies on this highly potential reaction were started only before 15 years. This review has been written to shed more lights to the importance of Baylis-Hillman reaction. We have focused mainly on the reaction mechanism, conceptually related reactions, and chemical transformations of the Baylis-Hillman adducts.
김정미,이상구,Se Hee Kim,이현승,김재녕 대한화학회 2008 Bulletin of the Korean Chemical Society Vol.29 No.11
Poly-substituted pyrrole derivatives were synthesized from Baylis-Hillman adducts via the following consecutive reactions comprised of (i) bromination of the Baylis-Hillman adduct, (ii) In-mediated Barbier reaction with aldehyde, (iii) PCC oxidation to α-methylene-γ-keto ester, (iv) reaction with amine to form enamine intermediate, (v) Michael type cyclization, and the final (vi) aerobic oxidation.
Kim, Ko-Hoon,Lee, Hyun-Seung,Kim, Sung-Hwan,Lee, Ka-Young,Lee, Ji-Eun,Kim, Jae-Nyoung Korean Chemical Society 2009 Bulletin of the Korean Chemical Society Vol.30 No.5
We developed an efficient three-step synthetic protocol of $\gamma$-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot $K_2CO_3$-mediated synthesis of $\gamma$-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.