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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >P-chiral 1-phosphanorbornenes: from asymmetric phospha-Diels-Alder reactions towards ligand design and functionalisation
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P-chiral 1-phosphanorbornenes: from asymmetric phospha-Diels-Alder reactions towards ligand design and functionalisation

机译：P-手性1-膦基降冰片烯：从不对称的Pha-Diels-Alder反应走向配体设计和功能化

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摘要

The principle of stereotopic face differentiation was successfully applied to 2H-phospholes which undergo a very efficient and highly stereoselective Diels-Alder reaction giving phosphorus-chiral 1-phosphanorbornenes with up to 87% yield. The observed reaction pathway has been supported by theoretical calculations showing that the cycloaddition reaction between 2H-phosphole 3a and the dienophile (5R)(-)- menthyloxy-2(5H)-furanone (8) is of normal electron demand. Optically pure phosphanes were obtained by separation of the single diastereomers and subsequent desulfurisation of the sulfur-protected phosphorus atom. Finally, divergent ligand synthesis is feasible by reduction of the chiral auxiliary, subsequent stereospecific intramolecular Michael addition, and various functionalisations of the obtained key compound 13a. Furthermore, the unique structural properties of phospanorbornenes are presented and compared to those of phosphanorbornanes.
机译：立体人脸分化原理已成功地应用于2H-磷脂，该2H-磷脂经过非常有效且高度立体选择性的Diels-Alder反应，产生的磷-手性1-膦基降冰片烯产率高达87％。观察到的反应路径已得到理论计算的支持，该理论表明2H-磷脂3a与亲双烯体（5R）（-）-薄荷氧基-2（5H）-呋喃酮（8）之间的环加成反应具有正常的电子需求。通过分离单个非对映异构体并随后将硫保护的磷原子脱硫获得光学纯的膦。最后，通过减少手性助剂，随后的立体特异性分子内迈克尔加成以及所获得的关键化合物13a的各种官能化，不同的配体合成是可行的。此外，提出了磷降冰片烯的独特结构性质，并将其与磷烷硼烷的性质进行了比较。

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