LDA-Catalyzed Cycloisomerization of 2-(2-Propynyloxy)ethyl Iodides Leading to 3-(Iodomethylene)tetrahydrofurans

LDA-Catalyzed Cycloisomerization of 2-(2-Propynyloxy)ethyl Iodides Leading to 3-(Iodomethylene)tetrahydrofurans

LDA catalyzes cycloisomerization of 2-(2-propynyloxy)ethyl iodides to give 3-(iodomethylene)tetrahydrofurans. The reaction is proposed to proceed through a mechanism involving exo-cyclization of an alkynyllithium intermediate and protonation of the resulting alkylidene carbenoid by the starting iodi...

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Veröffentlicht in:Organic letters 2005-03, Vol.7 (5), p.779-781
Hauptverfasser: Harada, Toshiro, Muramatsu, Keiko, Fujiwara, Takayuki, Kataoka, Hiroshi, Oku, Akira
Format: Artikel
Sprache:eng
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Zusammenfassung:LDA catalyzes cycloisomerization of 2-(2-propynyloxy)ethyl iodides to give 3-(iodomethylene)tetrahydrofurans. The reaction is proposed to proceed through a mechanism involving exo-cyclization of an alkynyllithium intermediate and protonation of the resulting alkylidene carbenoid by the starting iodide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol047570e