Samarium diiodide-promoted sequential coupling-aldol-reduction reactions of ferrocene-substituted enones

Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI:10.1016/S1387-1609(01)01257-9

Shean-Jeng Jong, Chao-Tsen Chen, Jim-Min Fang, Yi-Hong Liu, Gene-Hsiang Lee, Yu Wang

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引用次数: 2

Abstract

On treatment with SmI₂ in THF, 1-ferrocenyl-3-phenyl-2-propen-1-one and its related ferrocene-substituted enones underwent cyclodimerizations to give aldols (2a–g) with 3,4-trans configuration. Further reduction by using increased amounts of SmI₂ produced the corresponding diols. The stereoselectivity in this study was comparable with that in the SmI₂-promoted cyclodimerization of chalcones, but in contrast to that in the SmI₂-promoted cyclization-aldol reaction of 1,1’-dicinnamoylferrocenes. The thienyl- and furyl-substituted enones 5a and 5b could be visualized as an extended system of conjugated ketones, so that the SmI₂-mediated coupling reactions occurred preferably by linkages of β-carbons with thiophene or furan rings, giving compounds 8a,b and 9a,b.

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二碘化钐促进二茂铁取代烯酮的序贯偶联醛缩还原反应

sm2在THF中处理后，1-二茂铁基-3-苯基-2-丙烯-1- 1及其相关的二茂铁取代烯酮发生环二聚化反应，得到3,4-反式结构的醛醇(2a-g)。通过使用更多的SmI2进一步减少产生相应的二醇。本研究的立体选择性与smi2促进的查尔酮环二聚反应的立体选择性相当，但与smi2促进的1,1 ' -二氨基茂铁环化-醛醇反应的立体选择性不同。噻吩取代烯酮和呋喃取代烯酮5a和5b可以看作是共轭酮的扩展体系，因此smi2介导的偶联反应最好是通过β-碳与噻吩或呋喃环的连接进行的，得到化合物8a,b和9a,b。

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Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry

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