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.
D'Aniello, F., Mattii, D., Taddei, M. (1993). 2-(chloromethyl)-2-(trimethylsilyl)-1-propene - A Convenient Reagent For the Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones. SYNLETT, 1993(2), 119-121 [10.1055/s-1993-22369].
2-(chloromethyl)-2-(trimethylsilyl)-1-propene - A Convenient Reagent For the Synthesis of Methylenetetrahydrofurans and Methylenebutyrolactones
Taddei, Maurizio
1993-01-01
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.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/31037
Attenzione
Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo