金（I）催化从炔丙基酯合成（1E，3E）-二烯。
Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.
作者信息
Dudnik Alexander S, Schwier Todd, Gevorgyan Vladimir
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
出版信息
J Organomet Chem. 2009 Feb 15;694(4):482-485. doi: 10.1016/j.jorganchem.2008.08.010.
Abstract
A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.
摘要
已开发出一种温和且立体选择性的金（I）催化的炔丙基酯多米诺转化反应，可生成取代的（1E，3E）-二烯。该串联过程通过1,3-酰氧基或1,3-磷酸氧基迁移序列进行，以形成烯丙基中间体，随后进行质子转移。
相似文献
1
Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.金（I）催化从炔丙基酯合成（1E，3E）-二烯。
J Organomet Chem. 2009 Feb 15;694(4):482-485. doi: 10.1016/j.jorganchem.2008.08.010.
2
Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.金属催化的丙炔酸酯和磷酸酯的双迁移级联反应。
Chem Soc Rev. 2013 Jun 21;42(12):4991-5001. doi: 10.1039/c3cs35514d.
3
Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.机理多样的铜、银和金催化的酰氧基和磷酰氧基迁移：通过级联迁移/环异构化方法高效合成杂环化合物
J Am Chem Soc. 2007 Aug 15;129(32):9868-78. doi: 10.1021/ja072446m. Epub 2007 Jul 21.
4
The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.使用 Br/Cl 促进炔丙羧酸酯的区域选择性金催化重排：（1Z, 3E）-1-溴/氯-2-羧基-1,3-二烯的高效合成。
Chem Commun (Camb). 2010 Dec 28;46(48):9179-81. doi: 10.1039/c0cc03669b. Epub 2010 Oct 29.
5
Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates.金催化从炔丙基新戊酸酯合成（1Z，3E）-2-新戊酰氧基-1,3-二烯
J Am Chem Soc. 2008 Mar 26;130(12):3740-1. doi: 10.1021/ja800001h. Epub 2008 Mar 1.
6
Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.立体控制的 1,3-磷酸酯基和 1,3-卤原子迁移接力反应，得到高官能化的 1,3-二烯。
J Am Chem Soc. 2012 Apr 25;134(16):6928-31. doi: 10.1021/ja301243t. Epub 2012 Apr 12.
7
Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.通过1,3-酰氧基迁移/纳扎罗夫环化/羟醛加成串联反应实现金（I）催化的1,3-烯炔醛的立体选择性环化反应
Chem Sci. 2019 Jul 29;10(35):8219-8223. doi: 10.1039/c9sc02828e. eCollection 2019 Sep 21.
8
Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".铑催化炔丙酯在环加成反应中的酰氧基迁移，受近期“淘金热”的启发。
Chem Soc Rev. 2012 Dec 7;41(23):7698-711. doi: 10.1039/c2cs35235d.
9
1-(Triethoxysilyl)buta-1,3-dienes-New Building Blocks for Stereoselective Synthesis of Unsymmetrical (,)-1,4-Disubstituted 1,3-dienes.1-（三乙氧基甲硅烷基）-1,3-丁二烯——用于立体选择性合成不对称（，）-1,4-二取代1,3-丁二烯的新型构建单元
Materials (Basel). 2015 Oct 28;8(11):7250-7256. doi: 10.3390/ma8115378.
10
The effect of HSAB on stereoselectivity: copper- and gold-catalyzed 1,3-phosphatyloxy and 1,3-halogen migration relay to 1,3-dienes.硬软酸碱理论对立体选择性的影响：铜催化和金催化的1,3 - 磷酰氧基和1,3 - 卤素迁移重排至1,3 - 二烯。
J Org Chem. 2015 Feb 6;80(3):1661-71. doi: 10.1021/jo502600j. Epub 2015 Jan 16.
引用本文的文献
1
Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.铜、银和金催化的迁移环异构化反应合成杂环五元环。
Aldrichimica Acta. 2010;43(2):37-46.
2
Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.金属催化的丙炔酸酯和磷酸酯的双迁移级联反应。
Chem Soc Rev. 2013 Jun 21;42(12):4991-5001. doi: 10.1039/c3cs35514d.
3
Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.立体控制的 1,3-磷酸酯基和 1,3-卤原子迁移接力反应，得到高官能化的 1,3-二烯。
J Am Chem Soc. 2012 Apr 25;134(16):6928-31. doi: 10.1021/ja301243t. Epub 2012 Apr 12.
4
Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.高官能团化环己烯酮环的合成：铑催化的1,3-酰氧基迁移及随后的[5+1]环加成反应
Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1346-9. doi: 10.1002/anie.201006881. Epub 2010 Dec 29.
5
The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.使用 Br/Cl 促进炔丙羧酸酯的区域选择性金催化重排：（1Z, 3E）-1-溴/氯-2-羧基-1,3-二烯的高效合成。
Chem Commun (Camb). 2010 Dec 28;46(48):9179-81. doi: 10.1039/c0cc03669b. Epub 2010 Oct 29.
本文引用的文献
1
An Eldorado for Homogeneous Catalysis?均相催化的乐土？
Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4237-4239. doi: 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO;2-A.
2
Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.金催化的朝向萘的双重迁移-苯并环化串联反应。
Org Lett. 2008 Apr 3;10(7):1465-8. doi: 10.1021/ol800229h. Epub 2008 Mar 1.
3
Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates.金催化从炔丙基新戊酸酯合成（1Z，3E）-2-新戊酰氧基-1,3-二烯
J Am Chem Soc. 2008 Mar 26;130(12):3740-1. doi: 10.1021/ja800001h. Epub 2008 Mar 1.
4
Gold-catalyzed addition of carbon nucleophiles to propargyl carboxylates.金催化碳亲核试剂与炔丙基羧酸盐的加成反应。
Org Lett. 2007 Sep 27;9(20):4021-4. doi: 10.1021/ol701706d. Epub 2007 Sep 1.
5
Gold catalysts: towards sustainable chemistry.
Angew Chem Int Ed Engl. 2007;46(38):7154-6. doi: 10.1002/anie.200701622.
6
Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.机理多样的铜、银和金催化的酰氧基和磷酰氧基迁移：通过级联迁移/环异构化方法高效合成杂环化合物
J Am Chem Soc. 2007 Aug 15;129(32):9868-78. doi: 10.1021/ja072446m. Epub 2007 Jul 21.
7
Gold-catalyzed organic reactions.金催化的有机反应。
Chem Rev. 2007 Jul;107(7):3180-211. doi: 10.1021/cr000436x. Epub 2007 Jun 20.
8
From sigma- to pi-electrophilic Lewis acids. Application to selective organic transformations.从σ-亲电路易斯酸到π-亲电路易斯酸。在选择性有机转化中的应用。
J Org Chem. 2007 Oct 12;72(21):7817-31. doi: 10.1021/jo070579k. Epub 2007 Jun 19.
9
Gold-catalyzed efficient preparation of linear alpha-iodoenones from propargylic acetates.金催化从炔丙基乙酸酯高效制备线性α-碘代烯酮。
Org Lett. 2007 May 24;9(11):2147-50. doi: 10.1021/ol070637o. Epub 2007 Apr 28.
10
Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.串联金（I）催化的联烯基烯丙基环化/亲电环丙烷化反应
Org Lett. 2007 May 24;9(11):2207-9. doi: 10.1021/ol070788r. Epub 2007 Apr 25.
Zotero 插件