Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2018-03-03 DOI:10.1002/hc.21411

Péter Bagi, Kinga Juhász, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Elemér Fogassy, György Keglevich

引用次数: 0

Abstract

The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca²⁺-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (R,R)-spiro-TADDOL, or with the acidic Ca²⁺-salt of O,O′-dibenzoyl-(R,R)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.

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通过形成非对映体配合物制备对映纯1-异戊基-3-甲基-3-磷烯- 1-氧化物

研究了TADDOL衍生物和酒石酸衍生物的Ca2+盐通过形成非对映体络合物来分离1-异戊基-3-甲基-3-磷烯- 1-氧化物。用(R,R)-spiro- taddol或O,O ' -二苯甲酰-(R,R)-酒石酸的酸性Ca2+盐制备了1-异戊基-3-环氧膦烯的两种对映体。利用CD光谱和理论计算证实了负旋光度的1-异戊基-3-环氧膦对映体的绝对构型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.