由手性联苯酚催化的不对称Petasis反应。
Asymmetric petasis reactions catalyzed by chiral biphenols.
作者信息
Lou Sha, Schaus Scott E
机构信息
Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, USA.
出版信息
J Am Chem Soc. 2008 Jun 4;130(22):6922-3. doi: 10.1021/ja8018934. Epub 2008 May 7.
Abstract
Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral alpha-amino ester products are obtained in good yields (71-92%) and high enantiomeric ratios (89:11-98:2). Mechanistic investigations indicate single ligand exchange of acyclic boronate with VAPOL and tetracoordinate boronate intermediates.
摘要
手性联苯酚催化硼酸烯酯、仲胺和乙醛酸乙酯的对映选择性Petasis反应。该反应需要使用15 mol%的(S)-VAPOL作为催化剂，硼酸烯酯作为亲核试剂，乙醛酸乙酯作为醛组分，以及3A分子筛作为添加剂。手性α-氨基酯产物以良好的产率（71-92%）和高对映体比例（89:11-98:2）获得。机理研究表明无环硼酸酯与VAPOL发生单配体交换以及四配位硼酸酯中间体的形成。
相似文献
1
Asymmetric petasis reactions catalyzed by chiral biphenols.由手性联苯酚催化的不对称Petasis反应。
J Am Chem Soc. 2008 Jun 4;130(22):6922-3. doi: 10.1021/ja8018934. Epub 2008 May 7.
2
Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.手性联苯酚催化的不对称 Petasis-Borono-Mannich 烯丙基化反应。
Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1544-1548. doi: 10.1002/anie.201611332. Epub 2017 Jan 4.
3
Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.手性联苯酚催化的酚类、醛类和硼酸酯的对映选择性多组分缩合反应
Org Lett. 2015 Dec 4;17(23):5812-5. doi: 10.1021/acs.orglett.5b02954. Epub 2015 Nov 18.
4
Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.手性联苯酚催化的硼酸盐对邻醌甲醚的对映选择性加成。
J Am Chem Soc. 2012 Dec 12;134(49):19965-8. doi: 10.1021/ja309076g. Epub 2012 Dec 3.
5
Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.手性联苯酚催化硼酸酯对酰基亚胺的对映选择性加成反应。
Angew Chem Int Ed Engl. 2009;48(24):4337-40. doi: 10.1002/anie.200901023.
6
Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.通过催化无痕迹 Petasis 反应的对映选择性合成烯丙基。
J Am Chem Soc. 2017 Feb 8;139(5):1998-2005. doi: 10.1021/jacs.6b11937. Epub 2017 Jan 25.
7
Catalytic diastereoselective petasis reactions.催化非对映选择性佩替斯反应。
Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8172-5. doi: 10.1002/anie.201103271. Epub 2011 Jul 12.
8
Asymmetric allylboration of acyl imines catalyzed by chiral diols.手性二醇催化的酰基亚胺的不对称烯丙基硼化反应
J Am Chem Soc. 2007 Dec 12;129(49):15398-404. doi: 10.1021/ja075204v. Epub 2007 Nov 17.
9
Enantioselective organocatalytic three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids.手性有机催化的水杨醛、胺和硼酸酯的三组分 Petasis 反应。
Org Lett. 2012 Feb 17;14(4):976-9. doi: 10.1021/ol203109a. Epub 2012 Jan 31.
10
Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.手性联苯酚催化烯丙基硼酸酯不对称炔丙基化反应。
Org Lett. 2011 Aug 5;13(15):4020-3. doi: 10.1021/ol201535b. Epub 2011 Jul 6.
引用本文的文献
1
Strategic 1,n-migration of boronate complexes: a novel platform for remote C-C bond construction.策略1，硼酸酯配合物的n-迁移：一种用于远程碳-碳键构建的新型平台。
Mol Divers. 2025 Apr 2. doi: 10.1007/s11030-025-11169-8.
2
The Petasis Reaction: Applications and Organic Synthesis-A Comprehensive Review.彼得asis反应：应用与有机合成——全面综述
Top Curr Chem (Cham). 2025 Jan 25;383(1):7. doi: 10.1007/s41061-025-00491-2.
3
Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions.不对称和非定向Petasis反应的开发策略
Chemistry. 2024 Sep 2;30(49):e202401936. doi: 10.1002/chem.202401936. Epub 2024 Aug 12.
4
Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction.Petasis反应的最新趋势：对Petasis反应应用的新型催化合成方法的综述
Molecules. 2023 Dec 10;28(24):8032. doi: 10.3390/molecules28248032.
5
Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates.钯催化由乙醛酸、磺酰胺和芳基三氟硼酸盐对映选择性合成α-芳基甘氨酸衍生物
Beilstein J Org Chem. 2023 May 25;19:719-726. doi: 10.3762/bjoc.19.52. eCollection 2023.
6
Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of -arylglycine derivatives.钯催化乙醛酸、磺酰胺和芳基硼酸之间的不对称三组分反应合成α-芳基甘氨酸衍生物。
Front Chem. 2023 Mar 13;11:1165618. doi: 10.3389/fchem.2023.1165618. eCollection 2023.
7
Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether.由氨基烯酮硅基缩醛和氨基硅基烯醇醚衍生的亚胺盐的制备及其简便的加成反应
RSC Adv. 2020 Jul 24;10(46):27874-27883. doi: 10.1039/d0ra05768a. eCollection 2020 Jul 21.
8
Crown Ether-Derived Chiral BINOL: Enantioselective Michael Addition of Alkenyl Boronic Acids to α,β-Unsaturated Ketones.冠醚衍生的手性联萘酚：烯基硼酸对α,β-不饱和酮的对映选择性迈克尔加成反应
ACS Omega. 2021 Dec 10;6(50):35093-35103. doi: 10.1021/acsomega.1c05875. eCollection 2021 Dec 21.
9
Petasis vs. Strecker Amino Acid Synthesis: Convergence, Divergence and Opportunities in Organic Synthesis.Petasis 与 Strecker 氨基酸合成：有机合成中的趋同、发散与机遇。
Molecules. 2021 Mar 18;26(6):1707. doi: 10.3390/molecules26061707.
10
Synthesis and Reactivity of α-Haloglycine Esters: Hyperconjugation in Action.α-卤代甘氨酸酯的合成与反应性：超共轭作用
European J Org Chem. 2019 Oct 24;2019(39):6597-6605. doi: 10.1002/ejoc.201901033. Epub 2019 Aug 24.
本文引用的文献
1
Asymmetric allylboration of acyl imines catalyzed by chiral diols.手性二醇催化的酰基亚胺的不对称烯丙基硼化反应
J Am Chem Soc. 2007 Dec 12;129(49):15398-404. doi: 10.1021/ja075204v. Epub 2007 Nov 17.
2
Catalytic asymmetric synthesis of alpha-amino acids.α-氨基酸的催化不对称合成。
Chem Rev. 2007 Nov;107(11):4584-671. doi: 10.1021/cr050580o. Epub 2007 Oct 4.
3
Catalytic enantioselective petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst.新型设计的硫脲催化剂催化喹啉的催化对映选择性类Petasis反应。
J Am Chem Soc. 2007 May 30;129(21):6686-7. doi: 10.1021/ja071470x. Epub 2007 May 8.
4
Asymmetric conjugate alkenylation of enones catalyzed by chiral diols.手性二醇催化的烯酮不对称共轭烯基化反应
J Am Chem Soc. 2007 Apr 25;129(16):4908-9. doi: 10.1021/ja0713734. Epub 2007 Apr 3.
5
Asymmetric allylboration of ketones catalyzed by chiral diols.手性二醇催化的酮的不对称烯丙基硼化反应。
J Am Chem Soc. 2006 Oct 4;128(39):12660-1. doi: 10.1021/ja0651308.
6
Recent developments in isocyanide based multicomponent reactions in applied chemistry.应用化学中基于异腈的多组分反应的最新进展。
Chem Rev. 2006 Jan;106(1):17-89. doi: 10.1021/cr0505728.
7
Ligand-catalyzed asymmetric alkynylboration of enones: a new paradigm for asymmetric synthesis using organoboranes.配体催化的烯酮不对称炔基硼化反应：使用有机硼烷进行不对称合成的新范例。
J Am Chem Soc. 2005 Mar 16;127(10):3244-5. doi: 10.1021/ja043001q.
8
Asymmetric multicomponent reactions (AMCRs): the new frontier.不对称多组分反应（AMCRs）：新前沿
Angew Chem Int Ed Engl. 2005 Mar 4;44(11):1602-34. doi: 10.1002/anie.200460548.
9
New synthesis of vaulted biaryl ligands via the Snieckus phenol synthesis.通过斯涅库斯苯酚合成法实现拱形联芳基配体的新合成。
Org Lett. 2005 Feb 3;7(3):367-9. doi: 10.1021/ol047852e.
10
Recent developments in the catalytic asymmetric synthesis of alpha- and beta-amino acids.α-氨基酸和β-氨基酸催化不对称合成的最新进展。
Angew Chem Int Ed Engl. 2003 Sep 22;42(36):4290-9. doi: 10.1002/anie.200301600.
Zotero 插件