The Roles of 2-and 3-Axial Methoxy Groups in Determining the Stereochemistry of the Complex Metal Hydride Reduction of Cyclohexanones: Examination of the …

Y Senda, H Sakurai, S Nakano, H Itoh

Index: Senda, Yasuhisa; Sakurai, Hiroshi; Nakano, Shigeru; Itoh, Hiroki Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 11 p. 3297 - 3303

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Citation Number: 7

Abstract

The 2-and 3-axially substituted methoxy groups in cyclohexanones exhibit steric hindrance similar to that of the methyl group in LiAlH 4 and NaBH 4 reductions. The chelate complex formation between the zinc ion and the two oxygens in the molecule was suggested in the zinc borohydride reduction. The relative reactivities of cyclohexanones in which the 2-axial position is substituted by the methyl or the methoxy group in the LiAlH 4 reduction strongly ...