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Synlett 1999; 1999(2): 197-198
DOI: 10.1055/s-1999-2591
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The Chalcogeno-Baylis-Hillman Reaction of an α,β-Unsaturated Thioester: A New Approach to α-Methylene-β-hydroxy Carboxylic Acid Derivatives

T. Kataoka* , T. Iwama, H. Kinoshita, S. Tsujiyama, Y. Tsurukami, T. Iwamura, S. Watanabe
  • *Gifu Pharmaceutical University, 6-1, Mitahora-higashi 5-chome, Gifu 502 8585, Japan; Fax +81-58-2 37-59 79; E-mail: kataoka@gifu-pu.ac.jp
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Publication Date:
31 December 1999 (online)

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Treatment of aldehydes and an α,β-unsaturated thioester with a catalytic amount of Me2S in the presence of TiCl4 followed by Ti(O-i-Pr)4 or DBU gave α-methylene-β-hydroxy esters or thioesters, respectively, in moderate to good yields. DABCO and Bu3P were ineffective for the Baylis-Hillman reaction of a thioacrylate.

chalcogeno-Baylis-Hillman reaction - α,β-unsaturated thioester - α-methylene-β-hydroxy thioester - α-methylene-β-hydroxy ester

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