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羰基烯丙基化和巴豆基化：历史回顾、与聚酮化合物合成的相关性以及对映选择性钌催化氢自动转移过程的发展

Carbonyl Allylation and Crotylation: Historical Perspective, Relevance to Polyketide Synthesis, and Evolution of Enantioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer Processes.

作者信息

Ortiz Eliezer, Saludares Connor, Wu Jessica, Cho Yoon, Santana Catherine G, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry. 105 E 24 St. (A5300), Austin, Tx 78712-1167 (USA).

出版信息

Synthesis (Stuttg). 2023 May;55(10):1487-1496. doi: 10.1055/s-0042-1751420. Epub 2023 Feb 20.

DOI:10.1055/s-0042-1751420
PMID:37841289
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10569400/
Abstract

The evolution of methods for carbonyl allylation and crotylation of alcohol proelectrophiles culminating in the design of iodide-bound ruthenium-JOSIPHOS catalysts is prefaced by a brief historical perspective on asymmetric carbonyl allylation and its relevance to polyketide construction. Using gaseous allene or butadiene as precursors to allyl- or crotylruthenium nucleophiles, respectively, new capabilities for carbonyl allylation and crotylation have been unlocked, including stereo- and site-selective methods for the allylation and crotylation of 1,3-diols and related polyols.

摘要

醇亲电试剂羰基烯丙基化和巴豆酰化方法的发展最终促成了碘结合钌-JOSIPHOS催化剂的设计，在此之前先简要回顾了不对称羰基烯丙基化及其与聚酮化合物构建的相关性。分别使用气态丙二烯或丁二烯作为烯丙基钌或巴豆基钌亲核试剂的前体，羰基烯丙基化和巴豆酰化展现出了新的能力，包括1,3-二醇及相关多元醇烯丙基化和巴豆酰化的立体和位点选择性方法。

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本文引用的文献

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Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° vs 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.通过氢自动转移实现气态丙二烯不对称钌催化的羰基烯丙基化反应：用于简化聚酮化合物构建的一级醇与二级醇脱氢反应
ACS Catal. 2023 Feb 3;13(3):1662-1668. doi: 10.1021/acscatal.2c05425. Epub 2023 Jan 12.
2
Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.炔烃与羰基化合物及亚胺的对映选择性金属催化还原偶联：烯丙醇和烯丙胺的汇聚式构建
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