Accessing Phase-Transfer Catalysts and a Phosphoramidite Ligand via the Asymmetric Intramolecular Hydroamination Reaction,Organometallics

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Accessing Phase-Transfer Catalysts and a Phosphoramidite Ligand via the Asymmetric Intramolecular Hydroamination Reaction
Organometallics ( IF 2.5 ) Pub Date : 2023-05-30 , DOI: 10.1021/acs.organomet.3c00124
Daven Foster ₁ , Stephen A. Moggach ₁ , Reto Dorta ₁

Affiliation

Within the last few years, our group has developed the intramolecular, asymmetric hydroamination (HA) reaction to a point where essentially enantiopure products can be obtained. The question then arose as to whether we can apply the reaction in useful ways beyond the synthesis of natural/pharmaceutically relevant products. In the present paper, we incorporate a select few HA products for the production of new chiral phase-transfer catalysts. These species are synthesized in one or two synthetic steps from new spirocyclic HA products and are applied in a classical substitution reaction, showing negligible enantioselectivity. In a second application, we introduce a novel phosphoramidite ligand, obtained by combining BINOL (1,1′-bi-2-naphthol) and an optically pure HA product with phosphorous trichloride. The representative ligand shows high enantioselectivity and activity in the rhodium-catalyzed conjugate addition reaction (Hayashi–Miyaura reaction).

中文翻译：

通过不对称分子内氢氨化反应获得相转移催化剂和亚磷酰胺配体

在过去的几年里，我们的团队开发了分子内不对称氢胺化（HA）反应，基本上可以得到对映体纯的产品。接下来的问题是，除了天然/药物相关产品的合成之外，我们是否可以以有用的方式应用该反应。在本文中，我们结合了一些精选的 HA 产品来生产新型手性相转移催化剂。这些物质是由新的螺环 HA 产品通过一两个合成步骤合成的，并应用于经典的取代反应，显示出可忽略不计的对映选择性。在第二个应用中，我们介绍了一种新型亚磷酰胺配体，该配体是通过将 BINOL（1,1'-双-2-萘酚）和光学纯 HA 产品与三氯化磷结合而获得的。

更新日期：2023-05-30

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