生物异喹啉N，N'-二氧化氮催化丙基三氯硅烷对醛的对映选择性加成反应。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-11-25 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.255

Noble Brako, Sreerag Moorkkannur Narayanan, Amber Burns, Layla Auter, Valentino Cesiliano, Rajeev Prabhakar, Norito Takenaka

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引用次数: 0

摘要

首次制备了纯度为bb0 99%的丙基三氯硅烷，并通过系统的催化剂结构-反应性和选择性关系研究，建立了其催化醛的非对称区域特异性加成反应。所观察到的烯丙化反应的催化剂结构-对映选择性关系与类似的烯丙化反应完全相反。以61:39 ~ 92:8对映体比，得到11个α-烯丙醇，收率22 ~ 99%。此外，还对丙基三氯硅烷丙炔烯异构化的可能机理进行了计算研究。

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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Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N'-dioxide.

Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure-reactivity and selectivity relationship study. The observed catalyst structure-enantioselectivity relationship of the present allenylation reaction was found exactly opposite to that of the analogous allylation reaction. The method provided eleven α-allenic alcohols in 22-99% yield with 61:39-92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl-allenyl isomerization of propargyltrichlorosilane were computationally investigated.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.