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Synthesis 1995; 1995(10): 1305-1310
DOI: 10.1055/s-1995-4101
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Reaction of Ethyl α-Chloro-α-phenylselenoacetate with Alkenes: Synthesis of α-Phenylseleno-γ-Butyrolactones

Claudio C. Silveira* , Marcelo A. Araujo, Eder J. Lenardão, Antonio L. Braga, Miguel J. Dabdoub
  • *Departamento de Química, UFSM, 97119.900, Santa Maria, RS, Brazil
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Publication Date:
31 December 2000 (online)

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Ethyl α-chloro-α-phenylselenoacetate (1) reacts with alk-1-enes in the presence of TiCl4 to give the corresponding α-phenylseleno γ,δ-unsaturated esters. Reaction of 1 with di- and trisubstituted alkenes and SnCl4 as a Lewis acid affords γ-butyrolactones directly and a minor amount of the γ,δ-unsaturated esters. These esters were converted into γ-butyrolactones on hydrolysis and reaction with electrophiles.

Lewis acids - di- and trisubstituted alkenes - α-phenyl-seleno-γ-δ-unsaturated esters - γ-Butyrolactones