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Synlett 1997; 1997(8): 992-994
DOI: 10.1055/s-1997-926
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Stereoselective Reduction of Conjugated Homopropargylic Alcohols to (E)-Homoallylic Alcohols by Sodium Bis(2-methoxyethoxy) Aluminium Hydride

Benoit Crousse, Mouâd Alami* , Gérard Linstrumelle
  • *Ecole Normale Supérieure, Département de Chimie, 24 rue Lhomond, 75231 Paris Cedex 05, France, Fax: (+33) 01 44 32 33 25
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Publication History

Publication Date:
31 December 2000 (online)

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The reduction of various conjugated homopropargylic alcohols with sodium bis(2-methoxyethoxy) aluminium hydride (Red-Al®) in ether or THF is described. The reaction takes place cleanly and rapidly, under mild conditions, to give (E)-homoallylic alcohols stereoselectively in good isolated yields.

reduction - Red-Al® - homopropargylic alcohols - (E)-homoallylic alcohols - β-hydroxydienes - β-hydroxytrienes

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