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2005
Furan derivatives
R 0060
LDA-Catalyzed Cycloisomerization of 2-(2-Propynyloxy)ethyl Iodides Leading to
— The title reaction proceeds without loss of
30- 089 3-(Iodomethylene)tetrahydrofurans.
the iodo functional group. Furthermore, it takes place with higher stereoselectivity for
the formation of sterically less hindered (E) products than it is observed in the radical-mediated reactions. The attempt to cyclize the corresponding bromides fails
[cf. (Ib)]. The products can be used for the construction of complex carbon frameworks.
— (HARADA*, T.; MURAMATSU, K.; FUJIWARA, T.; KATAOKA, H.; OKU, A.;
Org. Lett. 7 (2005) 5, 779-781; Dep. Chem. Mater. Technol., Kyoto Inst. Technol.,
Sakyo, Kyoto 606, Japan; Eng.) — R. Steudel
2005
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