The conjugate addition of a silyl group to enones and its removal with copper(II) bromide: a protecting group for the αβ-unsaturation of αβ-unsaturated ketones

The conjugate addition of a silyl group to enones and its removal with copper(II) bromide: a protecting group for the αβ-unsaturation of αβ-unsaturated ketones
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甲硅烷基与烯酮的共轭加成及其用溴化铜(II)的去除:αβ-不饱和酮的αβ-不饱和的保护基团

DOI:
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发表时间:
1981
期刊:
影响因子:
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通讯作者:
S. K. Patel
S. K. Patel
中科院分区:
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文献类型:
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作者:
D. Ager;I. Fleming;S. K. Patel

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硅基锂试剂与铜(I)盐的混合物与烯酮(包括酯和醛)反应,以良好的产率得到β-硅基羰基化合物。β-甲硅烷基酮可用于合成而不会对甲硅烷基造成危险,烯酮基团可通过溴化-脱甲硅烷基溴化与溴化铜(II)还原。以香芹酮和二氢茉莉酮的合成为例说明了这一原理。
Silyl-lithium reagents mixed with copper(I) salts react with enones, including esters and aldehydes, to give β-silyl carbonyl compounds in good yield. The β-silylketones can be used in synthesis without risk to the silyl group and the enone group can be restored by bromination-desilylbromination with copper(II) bromide. The principle is illustrated with syntheses of carvone and dihydrojasmone.