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Synlett 1993; 1993(2): 119-121
DOI: 10.1055/s-1993-22369
DOI: 10.1055/s-1993-22369
letter
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2-(Chloromethyl)-2-(trimethylsilyl)-1-propene: A Convenient Reagent for the Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones
Further Information
Publication History
Publication Date:
19 March 2002 (online)
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.