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。
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.
机构信息
Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA.
出版信息
Chem Commun (Camb). 2010 Dec 28;46(48):9179-81. doi: 10.1039/c0cc03669b. Epub 2010 Oct 29.
Abstract
A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.
摘要
发展了一种使用含卤素炔烃的丙炔酸酯作为底物的金催化合成 1-溴/氯-2-羧基-1,3-二烯的方法。该反应具有高度的非对映选择性，炔烃末端的卤素原子选择性地促进 1,2-烷氧基迁移。二烯产物参与 Diels-Alder 和交叉偶联反应。
相似文献
1
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.
2
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.
3
Synthesis of Allahabadolactone A.Allahabadolactone A 的合成。
J Org Chem. 2017 Dec 1;82(23):12624-12630. doi: 10.1021/acs.joc.7b02368. Epub 2017 Nov 7.
4
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.
5
Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons.钌催化的二炔水合环化反应：取代1,3 - 二烯合成子的合成
Org Lett. 2005 May 26;7(11):2097-9. doi: 10.1021/ol0502937.
6
Atom-economical chemoselective synthesis of 1,4-enynes from terminal alkenes and propargylic alcohols catalyzed by Cu(OTf)2.铜(II)六氟硫酸盐催化末端烯烃和炔丙醇的原子经济性化学选择性合成 1,4-烯炔。
J Org Chem. 2013 Mar 15;78(6):2742-5. doi: 10.1021/jo3026803. Epub 2013 Feb 13.
7
Copper-catalyzed decarboxylative C-P cross-coupling of alkynyl acids with H-phosphine oxides: a facile and selective synthesis of (E)-1-alkenylphosphine oxides.铜催化的炔基酸与 H-膦氧化物的脱羧 C-P 交叉偶联：（E）-1-烯基膦氧化物的简便和选择性合成。
Org Lett. 2014 Sep 5;16(17):4464-7. doi: 10.1021/ol502009b. Epub 2014 Aug 21.
8
Alkyne elementometalation-Pd-catalyzed cross-coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: "green" way.炔烃元素金属化-Pd 催化交叉偶联。高效、选择性、经济且安全地合成所有可能类型的非循环烯烃，收率高：“绿色”方法。
J Org Chem. 2010 May 21;75(10):3151-82. doi: 10.1021/jo1003218.
9
Highly regio- and stereoselective intermolecular tandem reaction to synthesize chloro-substituted 1,3-butadienes.高区域和立体选择性的分子间串联反应合成氯取代的 1,3-丁二烯。
Chem Commun (Camb). 2010 Feb 21;46(7):1035-7. doi: 10.1039/b923464k. Epub 2010 Jan 14.
10
Highly enantioselective cyclopropenation reaction of 1-alkynes with α-alkyl-α-diazoesters catalyzed by dirhodium(II) carboxylates.由羧酸铑（II）催化的1-炔烃与α-烷基-α-重氮酯的高度对映选择性环丙烷化反应。
Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6803-8. doi: 10.1002/anie.201101905. Epub 2011 Jun 14.
引用本文的文献
1
Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.金（I）催化炔烃活化以构建分子复杂性。
Chem Rev. 2015 Sep 9;115(17):9028-72. doi: 10.1021/cr500691k. Epub 2015 Apr 6.
2
3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.3-酰氧基-1,4-烯炔：一种用于铑催化（5+2）环加成反应的新型五碳合成子。
Pure Appl Chem. 2014 Mar 1;86(3):409-417. doi: 10.1515/pac-2014-5042.
3
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.
4
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.
5
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.
6
Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.铑催化的 3-酰氧基-1,4-烯炔和炔烃的分子内和分子间[5+2]环加成反应以及伴随的 1,2-酰氧基迁移。
J Am Chem Soc. 2012 Mar 21;134(11):5211-21. doi: 10.1021/ja2109097. Epub 2012 Mar 12.
本文引用的文献
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
Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals.金、铂及其他亲电金属催化的炔烃与外部亲核试剂的碳环化反应
Chem Soc Rev. 2009 Aug;38(8):2269-81. doi: 10.1039/b807499m. Epub 2009 Apr 29.
3
Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.使用环丙烷探针进行金（I）催化的[3,3] - 迁移重排的机理研究。
J Am Chem Soc. 2009 Apr 1;131(12):4513-20. doi: 10.1021/ja900456m.
4
Ligand effects in homogeneous Au catalysis.均相金催化中的配体效应。
Chem Rev. 2008 Aug;108(8):3351-78. doi: 10.1021/cr068430g. Epub 2008 Jul 25.
5
Alternative synthetic methods through new developments in catalysis by gold.通过金催化的新进展实现的替代合成方法。
Chem Rev. 2008 Aug;108(8):3266-325. doi: 10.1021/cr068435d. Epub 2008 Jul 24.
6
Gold-catalyzed organic transformations.金催化的有机转化反应。
Chem Rev. 2008 Aug;108(8):3239-65. doi: 10.1021/cr068434l. Epub 2008 Jul 10.
7
Coinage metal-assisted synthesis of heterocycles.硬币金属辅助的杂环合成。
Chem Rev. 2008 Aug;108(8):3395-442. doi: 10.1021/cr050041j. Epub 2008 Jul 9.
8
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.
9
Golden carousel in catalysis: the cationic gold/propargylic ester cycle.催化中的金色旋转木马：阳离子金/炔丙基酯循环
Angew Chem Int Ed Engl. 2008;47(4):718-21. doi: 10.1002/anie.200703769.
10
Total synthesis of (+)-fawcettimine.（+）-法西梯明的全合成。
Angew Chem Int Ed Engl. 2007;46(40):7671-3. doi: 10.1002/anie.200702695.
Zotero 插件