Domino Michael-aldol annulations for the stereocontrolled synthesis of bicyclo[3.3.1]nonane and bicyclo[3.2.1]octane derivatives

被引：0

作者：

Promontorio R. ^{[1
,2
]}

Richard J.-A. ^{[1
]}

Marson C. ^{[2
]}

机构：

[1] Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros, #07-01, Singapore

[2] Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London

来源：

RSC Adv. | / 115卷 / 114412-114424期

关键词：

Ketones;

D O I：

10.1039/C6RA23523A

中图分类号：

学科分类号：

摘要：

Domino Michael-aldol annulation of cycloalkane-1,3-diones with enals affords a general route to 6-hydroxybicyclo[3.3.1]nonane-2,9-diones and 2-hydroxybicyclo[3.2.1]octane-6,8-diones, notably in one-pot procedures under convenient conditions. The annulation is shown to be compatible with one or more substituents at six positions of the bicyclo[3.3.1]nonane-2,9-dione scaffold. In some cases, the relative configuration of the product can be controlled by the appropriate choice of solvent, base and temperature for the annulation. In contrast to the chair-chair conformations usually adopted, the bicyclo compounds derived from 2,4,4-trimethylcyclohexane-1,3-dione possessed boat-chair conformations. Oxidation of the annulation products gave the corresponding bicyclo triketones. © The Royal Society of Chemistry.

引用

页码：114412 / 114424

页数：12

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