Role of the Heteroatoms in the Complex Metal Hydride Reduction of 2-t-Butyl-1,3-dioxan-5-one and 3-Oxoquinolizidine

The complex metal hydride reductions of 2-t-butyl-1,3-dioxan-5-one (1) and 3-oxoquinolizidine (3) are faster than those of the corresponding carbocyclic compounds, 4-t-butylcyclohexanone (2) and trans-2-decalone (4). The stereoselectivities were similar in the LiAlH4 reduction, but the heteracyclohe...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 72; no. 2; p. 285
Main Authors Senda, Yasuhisa, Sakurai, Hiroshi, Itoh, Hiroki
Format Journal Article
LanguageEnglish
Published Tokyo Chemical Society of Japan 01.02.1999
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Summary:The complex metal hydride reductions of 2-t-butyl-1,3-dioxan-5-one (1) and 3-oxoquinolizidine (3) are faster than those of the corresponding carbocyclic compounds, 4-t-butylcyclohexanone (2) and trans-2-decalone (4). The stereoselectivities were similar in the LiAlH4 reduction, but the heteracyclohexanones exhibited higher stereoselectivity with NaBH4. These facts are discussed in terms of the intramolecular orbital interaction.
ISSN:0009-2673
1348-0634