铂（II）催化氮丙啶基炔丙基酯合成1,2-二氢吡啶。
Pt(II)-catalyzed synthesis of 1,2-dihydropyridines from aziridinyl propargylic esters.
作者信息
Motamed Massoud, Bunnelle Eric M, Singaram Surendra W, Sarpong Richmond
机构信息
Department of Chemistry, University of California, Berkeley, California 94720, USA.
出版信息
Org Lett. 2007 May 24;9(11):2167-70. doi: 10.1021/ol070658i. Epub 2007 Apr 24.
Abstract
Pt(II)-catalyzed cycloisomerization of aziridinyl propargylic esters affords 1,2-dihydropyridines with regiodefined installation of substituents. A mild conversion of the 1,2-dihydropyridines to the corresponding substituted pyridines as well as chirality retention from the aziridinyl propargylic ester substrates have been demonstrated.
摘要
铂（II）催化氮丙啶基炔丙基酯的环异构化反应可提供具有区域选择性取代基的1,2 - 二氢吡啶。已证明1,2 - 二氢吡啶可温和转化为相应的取代吡啶，并且能从氮丙啶基炔丙基酯底物中保持手性。
相似文献
1
Pt(II)-catalyzed synthesis of 1,2-dihydropyridines from aziridinyl propargylic esters.铂（II）催化氮丙啶基炔丙基酯合成1,2-二氢吡啶。
Org Lett. 2007 May 24;9(11):2167-70. doi: 10.1021/ol070658i. Epub 2007 Apr 24.
2
Platinum-catalyzed cycloisomerization reaction of 1,6-enyne coupling with rearrangement of propargylic esters.铂催化的1,6-烯炔偶联与炔丙基酯重排的环异构化反应
J Org Chem. 2009 Jan 2;74(1):474-7. doi: 10.1021/jo802043z.
3
Synthesis of multiply substituted 1,6-dihydropyridines through Cu(I)-catalyzed 6-endo cyclization.通过铜（I）催化的6-内型环化反应合成多取代的1,6-二氢吡啶。
Org Biomol Chem. 2015 Jun 7;13(21):5955-63. doi: 10.1039/c5ob00356c.
4
Lewis acid-catalyzed cyclization of enaminones with propargylic alcohols: regioselective synthesis of multisubstituted 1,2-dihydropyridines.路易斯酸催化烯胺酮与丙炔醇的环化反应：多取代 1,2-二氢吡啶的区域选择性合成。
J Org Chem. 2013 Jun 7;78(11):5731-6. doi: 10.1021/jo4005553. Epub 2013 May 15.
5
Au(I)- and Pt(II)-catalyzed cycloetherification of omega-hydroxy propargylic esters.金（I）和铂（II）催化的ω-羟基炔丙基酯的环醚化反应
Org Lett. 2008 Jun 19;10(12):2533-6. doi: 10.1021/ol8008107.
6
Synthesis of α-Acyloxyketone Derivatives via the Platinum-Catalyzed Migration of Propargylic Esters.通过铂催化的炔丙基酯迁移合成α-酰氧基酮衍生物。
Chem Pharm Bull (Tokyo). 2015;63(9):710-9. doi: 10.1248/cpb.c15-00417.
7
Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.利用炔丙基酯原位生成金属卡宾进行铂催化的五元环化反应。
J Am Chem Soc. 2005 Sep 14;127(36):12468-9. doi: 10.1021/ja053192c.
8
Sc(OTf)3-catalyzed three-component cyclization of arylamines, β,γ-unsaturated α-ketoesters, and 1,3-dicarbonyl compounds for the synthesis of highly substituted 1,4-dihydropyridines and tetrahydropyridines.三组分环化反应
Sc(OTf)3 催化的三组分环化反应，包括芳胺、β,γ-不饱和α-酮酯和 1,3-二羰基化合物，用于合成高度取代的 1,4-二氢吡啶和四氢吡啶。
J Org Chem. 2013 Jun 7;78(11):5751-5. doi: 10.1021/jo400578m. Epub 2013 May 16.
9
Redox cycloisomerization approach to 1,2-dihydropyridines.1,2 - 二氢吡啶的氧化还原环异构化方法
Org Lett. 2015 Mar 20;17(6):1433-6. doi: 10.1021/acs.orglett.5b00279. Epub 2015 Mar 11.
10
Microwave-assisted copper(II)-catalyzed one-pot four-component synthesis of multifunctionalized dihydropyridines.微波辅助铜（II）催化的多功能二氢吡啶的一锅四组分合成
J Comb Chem. 2010 Jul 12;12(4):577-81. doi: 10.1021/cc100060s.
引用本文的文献
1
Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines.级联氮杂-Wittig/6π-电环化反应在 1,6-二氢吡啶合成中的应用。
Org Lett. 2021 Aug 6;23(15):6024-6029. doi: 10.1021/acs.orglett.1c02099. Epub 2021 Jul 22.
2
Au-Catalyzed Hexannulation and Pt-Catalyzed Pentannulation of Propargylic Ester Bearing a 2-Alkynyl-phenyl Substituent: A Comparative DFT Study.金催化的带有2-炔基苯基取代基的炔丙基酯的六元环化反应和铂催化的五元环化反应：一项比较性密度泛函理论研究
ACS Omega. 2018 Jan 29;3(1):1159-1169. doi: 10.1021/acsomega.7b01889. eCollection 2018 Jan 31.
3
Nickel-catalyzed enantioselective arylation of pyridine.镍催化吡啶的对映选择性芳基化反应。
Chem Sci. 2016 Jul 1;7(7):4105-4109. doi: 10.1039/c6sc00702c. Epub 2016 Mar 8.
本文引用的文献
1
Tetrasubstituted pyrrolidines via a tandem aza-Payne/hydroamination reaction.通过串联氮杂佩恩/氢胺化反应合成四取代吡咯烷
J Am Chem Soc. 2007 Apr 4;129(13):3794-5. doi: 10.1021/ja068077w. Epub 2007 Mar 10.
2
Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones.铂催化环化/1,2-迁移用于合成中氮茚、吡咯烷酮和中氮茚酮。
Org Lett. 2007 Mar 15;9(6):1169-71. doi: 10.1021/ol0701971. Epub 2007 Feb 20.
3
Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions.在亚胺 - 羟醛反应中使用乙烯基环氧乙烷作为掩蔽的烯醇负离子合成1,2 - 二氢吡啶。
Org Lett. 2006 Aug 3;8(16):3473-6. doi: 10.1021/ol061086p.
4
Pt-catalyzed tandem epoxide fragmentation/pentannulation of propargylic esters.铂催化的炔丙基酯的串联环氧化合物碎片化/戊环化反应
J Am Chem Soc. 2006 May 31;128(21):6786-7. doi: 10.1021/ja061549m.
5
Nucleophilic addition to 3-substituted pyridinium salts: expedient syntheses of (-)-L-733,061 and (-)-CP-99,994.对3-取代吡啶鎓盐的亲核加成反应：（-）-L-733,061和（-）-CP-99,994的简便合成方法
Org Lett. 2004 Sep 30;6(20):3517-20. doi: 10.1021/ol048624n.
6
New entries in Lewis acid-Lewis base bifunctional asymmetric catalyst: catalytic enantioselective Reissert reaction of pyridine derivatives.路易斯酸-路易斯碱双功能不对称催化剂的新进展：吡啶衍生物的催化对映选择性赖瑟特反应
J Am Chem Soc. 2004 Sep 29;126(38):11808-9. doi: 10.1021/ja045966f.
7
Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: application to the synthesis of (-)-coniine.2-取代二氢吡啶和哌啶的实用且高度区域和立体选择性合成：应用于（-）-coniine的合成。
J Am Chem Soc. 2001 Nov 28;123(47):11829-30. doi: 10.1021/ja017136x.
8
Quantitative structure-activity relationships for 1,4-dihydropyridine calcium channel antagonists (nifedipine analogues): a quantum chemical/classical approach.1,4-二氢吡啶类钙通道拮抗剂（硝苯地平类似物）的定量构效关系：一种量子化学/经典方法
J Pharm Sci. 1994 Aug;83(8):1110-5. doi: 10.1002/jps.2600830809.
Zotero 插件