铑催化的1,6-烯炔与对称和不对称炔烃的分子间[2+2+2]碳环化反应
Intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with symmetrical and unsymmetrical alkynes.
作者信息
Evans P Andrew, Sawyer James R, Lai Kwong Wah, Huffman John C
机构信息
Department of Chemistry, Indiana University, Bloomington, IN 47405, USA.
出版信息
Chem Commun (Camb). 2005 Aug 21(31):3971-3. doi: 10.1039/b505383h. Epub 2005 Jul 7.
Abstract
The crossed intermolecular rhodium-catalyzed [2+2+2] carbocyclization of carbon and heteroatom tethered 1,6-enynes can be accomplished with symmetrical and unsymmetrical alkynes, to afford the corresponding bicyclohexadienes in an efficient and highly selective manner.
摘要
碳和杂原子连接的1,6-烯炔的交叉分子间铑催化[2+2+2]碳环化反应可使用对称和不对称炔烃来完成，从而以高效且高选择性的方式得到相应的双环己二烯。
相似文献
1
Intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with symmetrical and unsymmetrical alkynes.铑催化的1,6-烯炔与对称和不对称炔烃的分子间[2+2+2]碳环化反应
Chem Commun (Camb). 2005 Aug 21(31):3971-3. doi: 10.1039/b505383h. Epub 2005 Jul 7.
2
Regio- and enantioselective intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with methyl arylpropiolates.铑催化的1,6-烯炔与芳基丙酸甲酯的区域和对映选择性分子间[2+2+2]碳环化反应
J Am Chem Soc. 2005 Sep 14;127(36):12466-7. doi: 10.1021/ja053123y.
3
Intermolecular rhodium-catalyzed [3+2+2] carbocyclization of alkenylidenecyclopropanes with activated alkynes: regio- and diastereoselective construction of cis-fused bicycloheptadienes.分子间铑催化的亚烷基环丙烷与活性炔烃的[3+2+2]碳环化反应：顺式稠合双环庚二烯的区域和非对映选择性构建
J Am Chem Soc. 2008 Oct 1;130(39):12838-9. doi: 10.1021/ja803691p. Epub 2008 Sep 9.
4
Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes.铑催化的炔烃偕碳金属化引发的1,5-烯炔的芳基化和烯基化环化反应
J Am Chem Soc. 2006 Dec 13;128(49):15598-9. doi: 10.1021/ja067125+.
5
Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.酯基对铑催化的 3-酰氧基-1,4-烯炔与炔烃的分子间[5+2]环加成反应的影响。
Chem Commun (Camb). 2013 Apr 4;49(26):2616-8. doi: 10.1039/c3cc40634b.
6
Rhodium-catalyzed [(3+2)+1] carbocyclization reactions of alkynylidenecyclopropanes with carbon monoxide: regiospecific construction of polysubstituted phenols.铑催化炔丙叉环丙烷与一氧化碳的 [(3+2)+1] 碳环化反应：多取代苯酚的区域选择性构建。
Org Lett. 2014 Sep 5;16(17):4356-9. doi: 10.1021/ol501724s. Epub 2014 Aug 11.
7
Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes.通过铑催化2-烯基苯酚与炔烃和烯炔的脱芳构化氧化环化反应合成螺环烯酮。
Chemistry. 2014 Jul 7;20(28):8599-602. doi: 10.1002/chem.201403454. Epub 2014 Jun 6.
8
Rhodium-Catalyzed (5 + 2) and (5 + 1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks.铑催化的以 1,4-烯炔为五碳砌块的（5 + 2）和（5 + 1）环加成反应
Acc Chem Res. 2020 Jan 21;53(1):231-243. doi: 10.1021/acs.accounts.9b00477. Epub 2019 Dec 10.
9
Regioselective synthesis of indenols by rhodium-catalyzed C-H activation and carbocyclization of aryl ketones and alkynes.通过铑催化芳基酮和炔烃的C-H活化及碳环化反应实现茚醇的区域选择性合成。
Angew Chem Int Ed Engl. 2011 Apr 26;50(18):4169-72. doi: 10.1002/anie.201100229. Epub 2011 Mar 29.
10
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.
引用本文的文献
1
The origin of the ligand-controlled regioselectivity in Rh-catalyzed [(2 + 2) + 2] carbocyclizations: steric stereoelectronic effects.铑催化的[(2 + 2) + 2]碳环化反应中配体控制的区域选择性的起源：空间和立体电子效应。
Chem Sci. 2015 Dec 1;6(12):6896-6900. doi: 10.1039/c5sc02307f. Epub 2015 Aug 25.
2
Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of -(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp)-H functionalization.-(2-乙炔基芳基)丙烯酰胺与叔烷基和仲烷基醛的分子间氧化脱羰[2 + 2 + 2]碳环化反应，涉及C(sp)-H官能团化。
Chem Sci. 2016 Dec 14;7(12):7050-7054. doi: 10.1039/c6sc02451c. Epub 2016 Jul 21.
3
Regio- and enantioselective intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with methyl arylpropiolates.铑催化的1,6-烯炔与芳基丙酸甲酯的区域和对映选择性分子间[2+2+2]碳环化反应
J Am Chem Soc. 2005 Sep 14;127(36):12466-7. doi: 10.1021/ja053123y.
本文引用的文献
1
A novel rhodium-catalyzed reduction-oxidation process: reaction of 4-alkynals with phenol to provide cis-4-alkenoates.一种新型铑催化的氧化还原过程：4-炔醛与苯酚反应生成顺式-4-烯酸酯。
Angew Chem Int Ed Engl. 2002 May 3;41(9):1607-9. doi: 10.1002/1521-3773(20020503)41:9<1607::aid-anie1607>3.0.co;2-q.
2
Iridium complex-catalyzed reaction of 1,6-enynes: cycloaddition and cycloisomerization.铱配合物催化的1,6-烯炔反应：环加成和环异构化
Org Lett. 2005 Apr 28;7(9):1711-4. doi: 10.1021/ol050085e.
3
Highly chemo- and regioselective intermolecular cyclotrimerization of alkynes catalyzed by cationic rhodium(I)/modified BINAP complexes.阳离子铑（I）/修饰的联萘酚配体（BINAP）配合物催化的炔烃的高度化学选择性和区域选择性分子间环三聚反应
Org Lett. 2003 Nov 27;5(24):4697-9. doi: 10.1021/ol035963s.
4
Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.金属介导的[2 + 2 + 2]环加成反应构建吡啶环
Chem Rev. 2003 Sep;103(9):3787-801. doi: 10.1021/cr030677f.
5
Rhodium-catalyzed [2 + 2 + 2] cyclotrimerization in an aqueous-organic biphasic system.铑催化的水-有机双相体系中的[2 + 2 + 2]环三聚反应。
J Am Chem Soc. 2003 Jul 2;125(26):7784-5. doi: 10.1021/ja035438o.
6
The behavior of 1,n-enynes in the presence of transition metals.1,n-烯炔在过渡金属存在下的行为。
Chem Rev. 2002 Mar;102(3):813-34. doi: 10.1021/cr980054f.
7
A versatile new method for the synthesis of cyclopentenones via an unusual rhodium-catalyzed intramolecular trans hydroacylation of an alkyne.
J Am Chem Soc. 2001 Nov 21;123(46):11492-3. doi: 10.1021/ja011907f.
8
Rhodium(I)-Catalyzed.铑（I）催化的
Angew Chem Int Ed Engl. 1999 Aug;38(16):2426-2430.
Zotero 插件