65080-77-5Relevant articles and documents
The Roles of 2- and 3-Axial Methoxy Groups in Determining the Stereochemistry of the Complex Metal Hydride Reduction of Cyclohexanones: Examination of the Cieplak Model
Senda, Yasuhisa,Sakurai, Hiroshi,Nakano, Shigeru,Itoh, Hiroki
, p. 3297 - 3303 (2007/10/03)
The 2- and 3-axially substituted methoxy groups in cyclohexanones exhibit steric hindrance similar to that of the methyl group in LiAlH4 and NaBH4 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 LiAlH4 reduction strongly support Cieplak's proposal, which focuses on the importance of the stabilization of the transition state by anti-periplanar allylic bonds.
