用二萘基对硫代膦酸酯醇解合成对立体硫代膦酸酯

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2018-11-17 DOI:10.1002/hc.21448

Kazuma Kuwabara, Yuuki Maekawa, Masahiro Ebihara, Toshifumi Maruyama, Toshiaki Murai

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引用次数: 3

摘要

带有二萘基的硫代膦酸盐与烷氧化合物的反应是通过将二萘基的轴向手性转移到磷原子的中心手性来得到具有中等至优异非对映选择性的p -立体硫代膦酸盐。膦酸盐的反应也以类似的方式进行。所得产物的硒原子可以用三甲基膦除去，得到三价膦酸盐，分离得到硼配合物。

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Synthesis of P-stereogenic phosphonothioates via alcoholysis of phosphonothioates with a binaphthyl group

The reaction of phosphonothioates having a binaphthyl group with alkoxides proceeded via transfer of the axial chirality of the binaphthyl group to the central chirality of the phosphorus atom to give P-stereogenic phosphonothioates with moderate-to-excellent diastereoselectivities. The reaction of phosphonoselenoates also proceeded in a similar fashion. The selenium atom of the obtained product could be excluded with tributylphosphine to give a trivalent phosphonite, which was isolated as a boron complex.

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.