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多酶一锅法立体选择性合成仲苄醇

Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols.

机构信息

University of Strasbourg, CNRS, ISIS UMR 7006, 8 Allée Gaspard Monge, 67000 Strasbourg, France.

出版信息

Org Lett. 2021 May 7;23(9):3502-3506. doi: 10.1021/acs.orglett.1c00939. Epub 2021 Apr 12.

DOI:10.1021/acs.orglett.1c00939
PMID:33844551
Abstract

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

摘要

一锅法程序有可能在无需连续中间体的分离和纯化的情况下,快速构建分子复杂性。在这里,我们报告了多催化方案,该方案在集成了烯烃交叉复分解、异构化和亲核加成的顺序催化下,将烯烃、不饱和脂肪醇和芳基硼酸高效立体选择性(通常 >95:5 er)地转化为仲苄基醇。前手性烯丙醇可以高立体选择性 (>98:2 er, >20:1 dr)转化为产物的任何立体异构体。

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Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols.多酶一锅法立体选择性合成仲苄醇
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引用本文的文献

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Variable structure diversification by multicatalysis: the case of alcohols.多相催化的可变结构多样化:醇的案例。
Chem Commun (Camb). 2023 Apr 18;59(32):4716-4725. doi: 10.1039/d3cc00551h.
2
Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.通过铑催化的合并转移氢化羰基加成-氧化还原异构化反应将伯醇和丁二烯转化为支链酮
J Am Chem Soc. 2021 Sep 1;143(34):13507-13512. doi: 10.1021/jacs.1c07230. Epub 2021 Aug 20.