Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenol

K Ishihara, N Hanaki, H Yamamoto

Index: Ishihara, Kazuaki; Hanaki, Naoyuki; Yamamoto, Hisashi Journal of the American Chemical Society, 1993 ,  vol. 115,  # 23  p. 10695 - 10704

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Citation Number: 41

Abstract

Abstract: Chiral acetals derived from aldehydes and (-)-(2R, 4R)-2, 4-pentanediol are cleaved selectively by organoaluminum reagents. The reaction proceeds via the retentive- alkylation process with> 95% selectivities in most cases. Trialkylaluminum reagent is utilized for higher alkyl transfers, but for smaller alkyl transfers, a new reagent system, combining trialkylaluminum and the halophenols such as pentafluorophenol and 2, 4, 6- ...