用于催化不对称氧化的多功能双异羟肟酸的开发与应用
Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation.
作者信息
Barlan Allan U, Zhang Wei, Yamamoto Hisashi
机构信息
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois, 60637, USA.
出版信息
Tetrahedron. 2007 Jul 2;63(27):6075-6087. doi: 10.1016/j.tet.2007.03.071.
Abstract
In this article, we describe the development and preliminary results of our new designed C(2)-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.
摘要
在本文中，我们描述了新设计的C(2)-对称双异羟肟酸（BHA）配体的开发及其初步结果，以及这些新配体在钒催化的烯丙醇和高烯丙醇不对称环氧化反应中的应用。基于这一成功，我们展示了BHA在钼催化的未官能化烯烃和硫化物不对称氧化反应中的多功能性。
相似文献
1
Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation.用于催化不对称氧化的多功能双异羟肟酸的开发与应用
Tetrahedron. 2007 Jul 2;63(27):6075-6087. doi: 10.1016/j.tet.2007.03.071.
2
Hydroxamic acids in asymmetric synthesis.羟胺在不对称合成中的应用。
Acc Chem Res. 2013 Feb 19;46(2):506-18. doi: 10.1021/ar300216r. Epub 2012 Nov 16.
3
Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols.催化对映选择性环氧化三级烯丙基和偕烯丙基醇。
J Am Chem Soc. 2013 Mar 6;135(9):3411-3. doi: 10.1021/ja401182a. Epub 2013 Feb 19.
4
Vanadium-catalyzed asymmetric epoxidation of allylic alcohols in water.水中钒催化的烯丙醇不对称环氧化反应
J Org Chem. 2009 May 1;74(9):3350-5. doi: 10.1021/jo900294h.
5
Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade.通过钒催化的不对称环氧化和开环级联反应对色氨酸进行去芳构化。
Chem Commun (Camb). 2014 Feb 7;50(10):1231-3. doi: 10.1039/c3cc47921h.
6
Bioinspired Manganese and Iron Complexes for Enantioselective Oxidation Reactions: Ligand Design, Catalytic Activity, and Beyond.仿生锰和铁配合物用于对映选择性氧化反应：配体设计、催化活性及其他。
Acc Chem Res. 2019 Aug 20;52(8):2370-2381. doi: 10.1021/acs.accounts.9b00285. Epub 2019 Jul 23.
7
Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation.氨基酸衍生的异羟肟酸作为钒催化环氧化反应中的手性配体。
Org Biomol Chem. 2005 Sep 7;3(17):3194-200. doi: 10.1039/b505324b. Epub 2005 Jul 27.
8
Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide.钨催化过氧化氢对烯丙基和偕烯丙基醇的不对称环氧化反应。
J Am Chem Soc. 2014 Jan 29;136(4):1222-5. doi: 10.1021/ja411379e. Epub 2014 Jan 21.
9
Hydrogen-bond-assisted epoxidation of homoallylic and allylic alcohols with hydrogen peroxide catalyzed by selenium-containing dinuclear peroxotungstate.含硒双核过氧钨酸盐催化的过氧化氢对高烯丙醇和烯丙醇的氢键辅助环氧化反应
J Am Chem Soc. 2009 May 27;131(20):6997-7004. doi: 10.1021/ja901289r.
10
Asymmetric epoxidation of allylic alcohols catalyzed by vanadium-binaphthylbishydroxamic Acid complex.钒-联萘双异羟肟酸配合物催化的烯丙醇不对称环氧化反应
J Org Chem. 2015 Mar 20;80(6):3203-10. doi: 10.1021/acs.joc.5b00185. Epub 2015 Mar 6.
引用本文的文献
1
Titanium cis-DACH Salan Catalyst for the Efficient Epoxidation of Nonactivated Olefins with Hydrogen Peroxide-Terminal-Selective Epoxidation of Multiply Unsaturated Terpenes.用于过氧化氢高效环氧化非活化烯烃的钛顺式-二氨基环己烷-Salan催化剂——多不饱和萜烯的末端选择性环氧化
Chemistry. 2025 Jul 11;31(39):e202501688. doi: 10.1002/chem.202501688. Epub 2025 Jun 22.
2
Direct N-O bond formation oxidation of amines with benzoyl peroxide.通过过氧化苯甲酰将胺直接氧化形成N-O键。
Chem Sci. 2018 Dec 12;10(7):2124-2129. doi: 10.1039/c8sc04996c. eCollection 2019 Feb 21.
3
Molybdenum-Catalyzed Enantioselective Sulfoxidation Controlled by a Nonclassical Hydrogen Bond between Coordinated Chiral Imidazolium-Based Dicarboxylate and Peroxido Ligands.钼催化的手性亚砜化反应通过配位手性咪唑二羧酸酯与过氧配体之间的非经典氢键控制。
Molecules. 2018 Jun 30;23(7):1595. doi: 10.3390/molecules23071595.
4
Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide.钨催化过氧化氢对烯丙基和偕烯丙基醇的不对称环氧化反应。
J Am Chem Soc. 2014 Jan 29;136(4):1222-5. doi: 10.1021/ja411379e. Epub 2014 Jan 21.
5
Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols.催化对映选择性环氧化三级烯丙基和偕烯丙基醇。
J Am Chem Soc. 2013 Mar 6;135(9):3411-3. doi: 10.1021/ja401182a. Epub 2013 Feb 19.
6
Hydroxamic acids in asymmetric synthesis.羟胺在不对称合成中的应用。
Acc Chem Res. 2013 Feb 19;46(2):506-18. doi: 10.1021/ar300216r. Epub 2012 Nov 16.
7
Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines.铪(IV)催化的 N-烯基砜和 N-对甲苯磺酰亚胺的对映选择性环氧化。
J Am Chem Soc. 2012 Mar 28;134(12):5440-3. doi: 10.1021/ja211880s. Epub 2012 Mar 20.
8
Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols.锆（IV）和铪（IV）催化的高对映选择性同烯丙基和双同烯丙基醇的环氧化反应。
J Am Chem Soc. 2010 Jun 16;132(23):7878-80. doi: 10.1021/ja100951u.
9
A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions.一种在环境条件下用高碘酸钠水溶液对芳香族和脂肪族环氧化合物进行C-C键裂解的简单方法。
Tetrahedron Lett. 2008 Apr 21;49(17):2764-2767. doi: 10.1016/j.tetlet.2008.02.142.
10
Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane.手性双氧乙烷对非共轭顺式烯烃的立体选择性环氧化。
Org Lett. 2009 Nov 19;11(22):5150-3. doi: 10.1021/ol901724v.
本文引用的文献
1
Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols.钒催化的高烯丙醇不对称环氧化反应。
J Am Chem Soc. 2007 Jan 17;129(2):286-7. doi: 10.1021/ja067495y.
2
Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum.钼的手性双异羟肟酸配合物催化烯烃的对映选择性氧化反应。
Angew Chem Int Ed Engl. 2006 Sep 4;45(35):5849-52. doi: 10.1002/anie.200601742.
3
Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.钒催化硫氧化/动力学拆分合成对映体纯的烷基芳基亚砜
Angew Chem Int Ed Engl. 2005 Nov 11;44(44):7221-3. doi: 10.1002/anie.200503046.
4
Ligand-accelerated vanadium-catalysed epoxidation in water.水中配体加速的钒催化环氧化反应
Chem Commun (Camb). 2005 Sep 28(36):4592-4. doi: 10.1039/b509436d. Epub 2005 Aug 19.
5
Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: an effective controller system and a rational mechanistic model.钒的手性配合物对烯丙醇的对映选择性环氧化：一种有效的控制体系和合理的机理模型。
Angew Chem Int Ed Engl. 2005 Jul 11;44(28):4389-91. doi: 10.1002/anie.200500938.
6
Investigations on the iron-catalyzed asymmetric sulfide oxidation.铁催化不对称硫化物氧化反应的研究
Chemistry. 2005 Feb 4;11(4):1086-92. doi: 10.1002/chem.200400857.
7
Efficient asymmetric oxidation of sulfides and kinetic resolution of sulfoxides catalyzed by a vanadium-salan system.钒-萨伦体系催化硫化物的高效不对称氧化及亚砜的动力学拆分
J Org Chem. 2004 Nov 26;69(24):8500-3. doi: 10.1021/jo040221d.
8
Olefin epoxidation with inorganic peroxides. Solutions to four long-standing controversies on the mechanism of oxygen transfer.无机过氧化物催化的烯烃环氧化反应：关于氧转移机理的四个长期争议的解决方案
Acc Chem Res. 2004 Sep;37(9):645-52. doi: 10.1021/ar0400140.
9
Organocatalytic asymmetric epoxidation of olefins by chiral ketones.手性酮催化的烯烃有机不对称环氧化反应
Acc Chem Res. 2004 Aug;37(8):488-96. doi: 10.1021/ar030063x.
10
Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions.
Angew Chem Int Ed Engl. 2004 Aug 13;43(32):4225-8. doi: 10.1002/anie.200460236.
Zotero 插件