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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 5
BKCSDE 30(5)
May 20, 2009 

Expedient One-Pot Synthesis of γ-Hydroxybutenolides Starting from Baylis-Hillman Adducts: Lactonization, Isomerization, and Aerobic Oxidation of α-Methylene-γ-hydroxyester
Ko Hoon Kim, Hyun Seung Lee, Sung Hwan Kim, Ka Young Lee, Ji Eun Lee, Jae Nyoung Kim*
Baylis-Hillman adducts, γ-Hydroxybutenolides, Hydroxylation, Lactones
We developed an efficient three-step synthetic protocol of γ-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot K2CO3-mediated synthesis of γ-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.
1012 - 1020
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