[1, 3]??Transfer of Chirality during the Nicholas Reaction in γ??Benzyloxy Propargylic Alcohols

DD Díaz, MA Ramírez, VS Martín

Index: Diaz, David D.; Ramirez, Miguel A.; Martin, Victor S. Chemistry - A European Journal, 2006 , vol. 12, # 9 p. 2593 - 2606

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Citation Number: 9

Abstract

Abstract A highly regio-and stereoselective intramolecular [1, 5]-hydrogen-transfer process is described. Treatment of γ-benzyl-protected Co 2 (CO) 6-α, γ-acetylenic diols with BF 3⋅ OEt 2 provides bis-homopropargylic alcohols. The reaction occurs within seconds, tolerates a wide range of functionalities, and provides good yields. When the ether group is located at a stereochemically defined carbon atom, the rearrangement occurs with high ...