2-(Chloromethyl)-2-(trimethylsilyl)-1-propene: A Convenient Reagent for the  Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones

Fabiana D'Aniello; Duccio Mattii; Maurizio Taddei

doi:10.1055/s-1993-22369

Synlett 1993; 1993(2): 119-121
DOI: 10.1055/s-1993-22369

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2-(Chloromethyl)-2-(trimethylsilyl)-1-propene: A Convenient Reagent for the Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones

Fabiana D'Aniello^* , Duccio Mattii, Maurizio Taddei

^*Dipartimento di Chimica Organica "Ugo Schiff', Università di Firenze, Via G. Capponi 9, I-50121 Firenze, Italy

Abstract

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The title reagent was used in reaction with aldehydes in the presence of BF₃ OEt₂ to give hydroxy allylic chlorides which were further transformed into tetrahydrofurans using DBU and LiClO₄. Alternatively butyrolactones could be prepared from the same intermediates after oxidation of the chloro allylic functionality. Starting from isoleucine we prepared a methylenebutyrolactone which has been used in the synthesis of several enzyme inhibitors.

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