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Synlett 1990; 1990(11): 701-703
DOI: 10.1055/s-1990-21217
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Diastereoselective Heteroconjugate Addition Using Phenylthioacetylene

Angkana Herunsalee* , Minoru Isobe, Yoshio Fukuda, Toshio Goto
  • *Laboratory of Organic Chemistry, School of Agriculture, Nagoya University, Chikusa, Nagoya 464, Japan
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Publication Date:
08 March 2002 (online)

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Phenylthioacetylene, as its lithium acetylide, was used for the opening of epoxides to afford 1-phenylthio-1-alkyn-4-ols. Hydrosilylation of the acetylene moiety was followed by oxidation of sulfur to give the corresponding 4-hydroxy-1-silyl-1-alkenyl sulfones, which act as the electrophile in heteroconjugate addition. Very high stereoselectivity is shown in the addition. The stereocontrolled processes are discussed.