Tetrahedron Letters p. 3829 - 3832 (1997)
Update date:2022-08-03
Topics:
Ma, Shengming
Liu, Fang
Negishi, Ei-Ichi
The reaction of ω-Me3Si- or ω-Me3Ge-substituted 3-butyn-1-ol, 4-pentyn-1-ol, and their derivatives with DIBAL-H and a small trialkylalane, e.g., Me3Al or Et3Al, at 23°C gives, after iodinolysis, the corresponding (Z)-4-iodo-3-buten-1-ols and (Z)-5-iodo-4-penten-1-ols in a highly stereo- and regio-selective manner, most probably via endo-dig mode cyclic anti-hydroalumination, while treatment of ω-carbosubstituted 3-butyn-1-ols with Red-Al or LialH4 at high temperatures followed by iodinolysis can give the corresponding (Z)-4-iodo-3-buten-1-ols also in a highly regio- and stereoselective manner.
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Doi:10.1016/S0960-894X(98)00556-3
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