Tetrahedron letters

Anti-hydroalumination of Homo-and bishomopropargyl alcohols

S Ma, F Liu, E Negishi

Index: Ma, Shengming; Liu, Fang; Negishi, Ei-Ichi Tetrahedron Letters, 1997 , vol. 38, # 22 p. 3829 - 3832

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Citation Number: 23

Abstract

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, eg, 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 ...

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