2-芳基色烯的催化对映选择性合成
Catalytic enantioselective synthesis of 2-aryl-chromenes.
作者信息
Zeng Bi-Shun, Yu Xinyi, Siu Paul W, Scheidt Karl A
机构信息
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.
出版信息
Chem Sci. 2014 Jun;5(6):2277-2281. doi: 10.1039/C4SC00423J.
Abstract
An enantioselective Pd-catalyzed 6--trig reaction for the synthesis of 2-aryl-chromenes has been developed. A systematic optimization of a TADDOL-derived ligand set resulted in the identification of a novel monodentate phosphoramidite-palladium catalyst that accesses 2-aryl--chromenes with high yield and enantioselectivity under mild conditions. The products obtained from this method can be transformed into biologically active compounds through functionalization of the chromene alkene.
摘要
已开发出一种用于合成2-芳基色烯的对映选择性钯催化6-三氟甲基化反应。对源自TADDOL的配体组进行系统优化，从而确定了一种新型单齿亚磷酰胺钯催化剂，该催化剂能在温和条件下以高收率和对映选择性得到2-芳基色烯。通过色烯烯烃的官能化，由该方法得到的产物可转化为生物活性化合物。
相似文献
1
Catalytic enantioselective synthesis of 2-aryl-chromenes.2-芳基色烯的催化对映选择性合成
Chem Sci. 2014 Jun;5(6):2277-2281. doi: 10.1039/C4SC00423J.
2
Pd(II)-Catalyzed Site-Selective Cross Coupling Reaction: Synthesis of Highly Fluorescent Aryl-Formyl-Chromenes and its Iminoantipyrine Analogues as Selective AChE Inhibitors.Pd(II) 催化的位点选择性交叉偶联反应：高荧光芳基甲酰色烯及其亚胺异喹啉类似物的合成作为选择性 AChE 抑制剂。
Chem Biodivers. 2024 Aug;21(8):e202400719. doi: 10.1002/cbdv.202400719. Epub 2024 Jul 3.
3
Brønsted acid catalyzed, conjugate addition of β-dicarbonyls to in situ generated ortho-quinone methides--enantioselective synthesis of 4-aryl-4H-chromenes.布朗斯特酸催化的β-二羰基化合物与原位生成的邻醌甲醚的共轭加成反应——4-芳基-4H-色烯的对映选择性合成。
Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7923-7. doi: 10.1002/anie.201403573. Epub 2014 Jun 18.
4
Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine.钯催化的单齿膦酰胺配体对映选择性 Heck 羰基化反应：（+）-石杉堿、（+）-石杉堿乙、和（+）-佛卡坦碱的不对称合成。
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):12199-12205. doi: 10.1002/anie.202003288. Epub 2020 May 18.
5
Enantioselective palladium(0)-catalyzed Nazarov-type cyclization.对映选择性钯（0）催化 Nazarov 型环化反应。
Angew Chem Int Ed Engl. 2015 May 18;54(21):6288-91. doi: 10.1002/anie.201500881. Epub 2015 Apr 1.
6
Palladium(II)-Catalyzed Enantioselective Reactions Using COP Catalysts.钯(II)催化的使用 COP 催化剂的对映选择性反应。
Acc Chem Res. 2016 Oct 18;49(10):2220-2231. doi: 10.1021/acs.accounts.6b00398. Epub 2016 Sep 30.
7
Y(OTf)-catalyzed phosphorylation of 2H-chromene hemiacetals with P(O)-H compounds to 2-phosphorylated 2H-chromenes.Y(OTf)-催化 2H-色烯半缩醛与 P(O)-H 化合物的磷酸化反应生成 2-磷酸化 2H-色烯。
Org Biomol Chem. 2021 Aug 21;19(31):6812-6816. doi: 10.1039/d1ob01221e. Epub 2021 Jul 23.
8
Reaction Optimization, Scalability, and Mechanistic Insight on the Catalytic Enantioselective Desymmetrization of 1,1-Diborylalkanes via Suzuki-Miyaura Cross-Coupling.通过铃木-宫浦交叉偶联实现1,1-二硼基烷烃催化对映选择性去对称化的反应优化、可扩展性及机理洞察
Chemistry. 2015 Dec 21;21(52):19186-94. doi: 10.1002/chem.201406680. Epub 2015 Apr 1.
9
Enantioselective -Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles.通过C1-铵烯醇盐亲核试剂实现芳基乙酸酯的对映选择性烯丙基化反应：用于缺电子亲电试剂的一种广泛有效的钯催化剂的鉴定
ACS Catal. 2018 Nov 2;8(11):10537-10544. doi: 10.1021/acscatal.8b03507. Epub 2018 Sep 27.
10
Catalyst-Controlled Divergent Synthesis of 2-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones.通过乙烯基硫鎓叶立德与醌的[3 + 3]环化反应实现催化剂控制的2-色烯的发散合成。
Org Lett. 2024 Feb 2;26(4):809-813. doi: 10.1021/acs.orglett.3c03894. Epub 2024 Jan 23.
引用本文的文献
1
Investigation of the Effect of Solvents on the Synthesis of Aza-flavanone from Aminochalcone Facilitated by Halogen Bonding.卤键促进下溶剂对由氨基查尔酮合成氮杂黄烷酮影响的研究
ACS Omega. 2023 Sep 1;8(37):33785-33793. doi: 10.1021/acsomega.3c04207. eCollection 2023 Sep 19.
2
Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity.通过铜催化色烯的动力学拆分实现黄烷醇的不对称合成及其抗炎活性。
Sci Adv. 2022 Jun 3;8(22):eabm9603. doi: 10.1126/sciadv.abm9603.
3
Synthesis of substituted 2H-chromenes by a three-component reaction as potential antioxidants.通过三组分反应合成取代的 2H-色烯作为潜在的抗氧化剂。
Mol Divers. 2017 Nov;21(4):841-848. doi: 10.1007/s11030-017-9758-3. Epub 2017 Jun 20.
本文引用的文献
1
One-point binding ligands for asymmetric gold catalysis: phosphoramidites with a TADDOL-related but acyclic backbone.用于不对称金催化的单点结合配体：具有 TADDOL 相关但非环骨架的磷酰胺。
J Am Chem Soc. 2012 Sep 19;134(37):15331-42. doi: 10.1021/ja303641p. Epub 2012 Sep 11.
2
Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.镍催化的色烯缩醛与硼酸的交叉偶联反应。
Org Lett. 2012 Mar 16;14(6):1616-9. doi: 10.1021/ol300364s. Epub 2012 Mar 2.
3
Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (-)-epicatechin gallate.（-）-表儿茶素没食子酸酯结构类似物的抗葡萄球菌活性和β-内酰胺类抗生素耐药性减弱能力。
Bioorg Med Chem Lett. 2011 Dec 1;21(23):6996-7000. doi: 10.1016/j.bmcl.2011.09.116. Epub 2011 Oct 8.
4
Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.高对映选择性布朗斯台德酸催化的螺环吲哚吡喃合成。
Org Lett. 2011 Jun 17;13(12):3086-9. doi: 10.1021/ol200987c. Epub 2011 May 18.
5
Synthesis of (-)-okilactomycin by a Prins-type fragment-assembly strategy.通过普林斯型片段组装策略合成（-）-奥基拉霉素。
Angew Chem Int Ed Engl. 2011 Jun 20;50(26):5892-5. doi: 10.1002/anie.201102037. Epub 2011 May 10.
6
Chiral organic contact ion pairs in metal-free catalytic asymmetric allylic substitutions.手性有机接触离子对在非均相催化不对称烯丙基取代反应中的应用。
J Am Chem Soc. 2011 Mar 23;133(11):3732-5. doi: 10.1021/ja110213t. Epub 2011 Feb 28.
7
Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression.阿比西酮的简洁合成以及前列腺癌和基质金属蛋白酶-2表达新抑制剂的发现。
ACS Med Chem Lett. 2010 Nov 11;1(8):400-405. doi: 10.1021/ml100110x.
8
Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.钯催化乙烯基氮杂环丙烷与氮杂环的动态动力学不对称转化：快速获得生物活性的吡咯和吲哚。
J Am Chem Soc. 2010 Nov 10;132(44):15800-7. doi: 10.1021/ja1071509.
9
A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes.一种用于取代色烯合成的高适应性催化剂/底物系统。
Chem Commun (Camb). 2010 Sep 28;46(36):6849-51. doi: 10.1039/c0cc01961e. Epub 2010 Aug 20.
10
Enantioselective addition of boronates to chromene acetals catalyzed by a chiral Brønsted acid/Lewis acid system.手性 Brønsted 酸/路易斯酸体系催化硼酸盐对色烯缩醛的对映选择性加成。
Angew Chem Int Ed Engl. 2010 Sep 17;49(39):7096-100. doi: 10.1002/anie.201003469.
Zotero 插件