2-(Chloromethyl)-2-(trimethylsilyl)-1-propene: A Convenient Reagent for the Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones
- 1 January 1993
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1993 (02) , 119-121
- https://doi.org/10.1055/s-1993-22369
Abstract
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.Keywords
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