通过不对称氢甲酰化苯乙烯衍生物合成 4-甲基-3,4-二氢异香豆素
Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.
机构信息
Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.
Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104 , United States.
出版信息
J Org Chem. 2019 Apr 19;84(8):4915-4920. doi: 10.1021/acs.joc.8b02813. Epub 2019 Mar 6.
Abstract
Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.
摘要
通过使用 BIBOP 型配体对苯乙烯衍生物进行不对称氢甲酰化反应，可以得到对映体富集的醛。其中一个典型的例子是通过不对称氢甲酰化乙基 2-乙烯基苯甲酸酯，随后在还原过程中进行原位内酯化反应，以 95.1:4.9 的对映体比例制备得到 4-甲基-3,4-二氢异香豆素。这些条件与富电子和缺电子取代基都兼容。
相似文献
1
Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.通过不对称氢甲酰化苯乙烯衍生物合成 4-甲基-3,4-二氢异香豆素
J Org Chem. 2019 Apr 19;84(8):4915-4920. doi: 10.1021/acs.joc.8b02813. Epub 2019 Mar 6.
2
An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids.通过苯乙烯型羧酸的溴环化反应实现 3,4-二氢异香豆素的对映选择性方法。
J Org Chem. 2012 Jan 20;77(2):999-1009. doi: 10.1021/jo202221c. Epub 2011 Dec 29.
3
A hybrid phosphorus ligand for highly enantioselective asymmetric hydroformylation.一种用于高对映选择性不对称氢甲酰化反应的混合磷配体。
J Am Chem Soc. 2006 Jun 7;128(22):7198-202. doi: 10.1021/ja057065s.
4
Rh-catalyzed linear hydroformylation of styrene.铑催化苯乙烯线性加氢甲酰化反应。
Dalton Trans. 2013 Jan 7;42(1):137-42. doi: 10.1039/c2dt31738a.
5
Enantioselective hydroformylation by a Rh-catalyst entrapped in a supramolecular metallocage.超分子金属笼中铑催化剂的对映选择性氢甲酰化作用。
J Am Chem Soc. 2015 Feb 25;137(7):2680-7. doi: 10.1021/ja512637k. Epub 2015 Feb 11.
6
Synthesis and application of modular phosphine-phosphoramidite ligands in asymmetric hydroformylation: structure-selectivity relationship.模块化膦-磷酰胺配体在不对称氢甲酰化反应中的合成与应用：结构-选择性关系。
Chemistry. 2010 Jan 18;16(3):871-7. doi: 10.1002/chem.200902238.
7
Highly regioselective hydroformylation of styrene and its derivatives catalyzed by Rh complex with tetraphosphorus ligands.铑配合物与四磷配体催化苯乙烯及其衍生物的高区域选择性氢甲酰化反应。
Org Lett. 2009 Jan 1;11(1):241-4. doi: 10.1021/ol802479y.
8
Reversal of enantioselectivity in the hydroformylation of styrene with [2S,4S-BDPP]Pt(SnCl3)Cl at high temperature arises from a change in the enantioselective-determining step.在高温下，使用[2S,4S - BDPP]Pt(SnCl₃)Cl对苯乙烯进行氢甲酰化反应时，对映选择性的反转源于对映选择性决定步骤的改变。
J Am Chem Soc. 2004 May 5;126(17):5585-92. doi: 10.1021/ja0318479.
9
Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation.通过铑（I）-（R，S）-联萘膦催化的不对称氢甲酰化反应及随后的氧化反应合成α-杂芳基丙酸
J Org Chem. 2007 Nov 9;72(23):8671-6. doi: 10.1021/jo0712190. Epub 2007 Oct 10.
10
Rh-catalyzed asymmetric hydroformylation of functionalized 1,1-disubstituted olefins.铑催化的官能化 1,1-二取代烯烃不对称氢甲酰化反应。
J Am Chem Soc. 2011 Nov 30;133(47):19080-3. doi: 10.1021/ja2092689. Epub 2011 Nov 7.
本文引用的文献
1
Recent Developments in the Scope, Practicality, and Mechanistic Understanding of Enantioselective Hydroformylation.对映选择性氢甲酰化反应在范围、实用性及机理理解方面的最新进展
Acc Chem Res. 2018 Sep 18;51(9):2344-2354. doi: 10.1021/acs.accounts.8b00335. Epub 2018 Aug 17.
2
Understanding a Hydroformylation Catalyst that Produces Branched Aldehydes from Alkyl Alkenes.理解一种氢甲酰化催化剂，它能将烷基烯烃转化为支链醛。
J Am Chem Soc. 2017 Nov 8;139(44):15921-15932. doi: 10.1021/jacs.7b09164. Epub 2017 Oct 25.
3
Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model.用扭曲/相互作用-激活应变模型分析反应速率。
Angew Chem Int Ed Engl. 2017 Aug 14;56(34):10070-10086. doi: 10.1002/anie.201701486. Epub 2017 Jul 17.
4
Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins.钌-NHC-二胺催化的异香豆素的对映选择性氢化。
J Am Chem Soc. 2017 Feb 22;139(7):2585-2588. doi: 10.1021/jacs.6b13124. Epub 2017 Feb 8.
5
Unexpected CO Dependencies, Catalyst Speciation, and Single Turnover Hydrogenolysis Studies of Hydroformylation via High Pressure NMR Spectroscopy.通过高压 NMR 光谱研究高压下通过高压 NMR 光谱研究氢甲酰化反应中的意外 CO 依赖性、催化剂形态和单程氢解
J Am Chem Soc. 2017 Feb 22;139(7):2778-2785. doi: 10.1021/jacs.6b12533. Epub 2017 Feb 8.
6
Tunable P-Chiral Bisdihydrobenzooxaphosphole Ligands for Enantioselective Hydroformylation.手性双二氢苯并氧杂磷杂环戊烯配体的可调性及其在手性氢甲酰化反应中的应用。
Org Lett. 2016 Jul 15;18(14):3346-9. doi: 10.1021/acs.orglett.6b01452. Epub 2016 Jun 22.
7
Organocatalytic Aerobic Oxidation of Benzylic sp(3) C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst.可循环使用的TEMPO催化剂促进的醚类和烷基芳烃苄基sp(3) C-H键的有机催化需氧氧化反应
Org Lett. 2015 Nov 6;17(21):5492-5. doi: 10.1021/acs.orglett.5b02877. Epub 2015 Oct 29.
8
Interception and characterization of catalyst species in rhodium bis(diazaphospholane)-catalyzed hydroformylation of octene, vinyl acetate, allyl cyanide, and 1-phenyl-1,3-butadiene.铑双(二氮杂环戊烯基)催化辛烯、醋酸乙烯酯、丙烯腈和 1-苯基-1,3-丁二烯的加氢甲酰化中催化剂物种的截获和表征。
J Am Chem Soc. 2015 Nov 11;137(44):14208-19. doi: 10.1021/jacs.5b09858. Epub 2015 Nov 2.
9
Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand.使用商业化的Ph-BPE配体对1-烯烃进行对映选择性氢甲酰化反应。
Org Lett. 2015 Jul 2;17(13):3264-7. doi: 10.1021/acs.orglett.5b01421. Epub 2015 Jun 19.
10
Asymmetric hydroformylation of Z-enamides and enol esters with rhodium-bisdiazaphos catalysts.手性双氮杂菲铑配合物催化 Z-烯酰胺和烯醇酯的不对称氢甲酰化反应。
J Am Chem Soc. 2014 Oct 15;136(41):14583-8. doi: 10.1021/ja507701k. Epub 2014 Oct 2.
Zotero 插件