Reduction of Cyclic and Bicyclicc Ketones by Complex Metal Hydrides

Boone, James L.; Ashby, E. C.

doi:10.1002/9780470147207.ch2

Cited by 64 publications

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“…From the 2- tert -butylcyclohexanone (Table , entry 6), a 50/50 mixture of isomers was formed. In fact, it has been shown that there is only a slight difference between the two faces of the carbonyl group due to the twisted conformation of this ketone and therefore a more hindered catalyst is needed to observe a diastereoselectivity . Silylated products formed from trimethylcyclohexanone, fenchone, and camphor (Table , entries 4, 9, and 10) presented a major diastereoisomer but this diastereoselectivity can be explained by the structure of the starting material.…”

Section: Resultsmentioning

confidence: 99%

A Simple and Efficient Copper-Catalyzed Procedure for the Hydrosilylation of Hindered and Functionalized Ketones

et al. 2005

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The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC.HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

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Section: Resultsmentioning

confidence: 99%