通过缺电子的2-硅氧基甲基苯乙炔衍生物的氟化物诱导环化合成亚烷基苯酞
Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.
作者信息
Duan Shaofeng, Cress Karen, Waynant Kris, Ramos-Miranda Elias, Herndon James W
机构信息
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003, USA.
出版信息
Tetrahedron. 2007 Apr 2;63(14):2959-2965. doi: 10.1016/j.tet.2007.01.046.
Abstract
Fluoride-based deprotection of silylated 2-alkynylbenzyl alcohol derivatives featuring carbonyl-substituted alkynes results in the direct synthesis of alkylidenephthalan vinylogous esters. The reaction is selective for the Z alkylidenephthalans in a thermodynamically controlled process. Similar compounds are also produced in the coupling of Fischer carbene complexes with 2-alkynylbenzoyl derivatives in an aqueous solvent system. Subsequent acid-catalyzed inter- or intramolecular Diels-Alder reactions lead to hydronaphthalene or hydrophenanthrene derivatives.
摘要
以羰基取代的炔烃为特征的甲硅烷基化2-炔基苄醇衍生物的氟化物脱保护反应可直接合成亚烷基萘并苯乙烯基酯。该反应在热力学控制的过程中对Z-亚烷基萘并苯具有选择性。在水性溶剂体系中，费歇尔卡宾配合物与2-炔基苯甲酰衍生物的偶联反应也能生成类似的化合物。随后的酸催化分子间或分子内狄尔斯-阿尔德反应可生成氢化萘或氢化菲衍生物。
相似文献
1
Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.
Tetrahedron. 2007 Apr 2;63(14):2959-2965. doi: 10.1016/j.tet.2007.01.046.
2
Synthesis of hydronaphthalenes through coupling of enyne carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes.
Tetrahedron Lett. 2010 May 20;51(28):3682-3684. doi: 10.1016/j.tetlet.2010.05.049.
3
Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives.
Org Lett. 2000 May 4;2(9):1267-9. doi: 10.1021/ol005691i.
4
Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes.
Tetrahedron Lett. 2017 Apr 5;58(14):1403-1407. doi: 10.1016/j.tetlet.2017.02.070. Epub 2017 Feb 24.
5
Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates.
Org Lett. 2008 Apr 17;10(8):1541-4. doi: 10.1021/ol800242n. Epub 2008 Mar 20.
6
A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes.
J Am Chem Soc. 2007 Nov 21;129(46):14422-6. doi: 10.1021/ja075106+. Epub 2007 Oct 30.
7
Synthesis of benzocycloheptanones through coupling of δ,ε-unsaturated chromium carbene complexes and 2-alkynylbenzoyl derivatives.
Org Lett. 2011 Jun 3;13(11):2848-51. doi: 10.1021/ol200825j. Epub 2011 May 9.
8
Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a Diels-Alder approach.
J Am Chem Soc. 2007 Jul 25;129(29):9109-16. doi: 10.1021/ja071163r. Epub 2007 Jun 29.
9
[The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds].
Yakugaku Zasshi. 2003 Sep;123(9):717-59. doi: 10.1248/yakushi.123.717.
10
Synthesis of furano[2,3-c]pyran-3-one and thieno[2,3-c]pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes: total synthesis of a Baccharis-derived cadinene derivative.
J Org Chem. 2002 Jun 14;67(12):4177-85. doi: 10.1021/jo011136y.
引用本文的文献
1
The [5+5] route to the phenanthrene skeleton.
ARKIVOC. 2016;2016(1):276-306. doi: 10.3998/ark.5550190.p009.611. Epub 2016 Jun 21.
2
Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.
Org Lett. 2012 Jul 6;14(13):3264-7. doi: 10.1021/ol301154f. Epub 2012 Jun 21.
3
Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer-carbene complex coupling and inter- or intramolecular Diels-Alder reactions.
Tetrahedron Lett. 2011 Aug 10;52(32):4182-4185. doi: 10.1016/j.tetlet.2011.06.006.
4
Synthesis of benzocycloheptanones through coupling of δ,ε-unsaturated chromium carbene complexes and 2-alkynylbenzoyl derivatives.
Org Lett. 2011 Jun 3;13(11):2848-51. doi: 10.1021/ol200825j. Epub 2011 May 9.
5
Electronic Control of Product Distribution in the [5+5]-Coupling of ortho-Alkynylbenzaldehyde Derivatives and γ,δ-Unsaturated Carbene Complexes.
Tetrahedron. 2010 Jul;66(27-28):4954-4960. doi: 10.1016/j.tet.2010.04.117.
本文引用的文献
1
Total synthesis of antofine using the net [5+5]-cycloaddition of gamma,delta-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step.
J Org Chem. 2006 Aug 18;71(17):6682-5. doi: 10.1021/jo061053n.
2
Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones.
J Am Chem Soc. 2006 Aug 2;128(30):9661-7. doi: 10.1021/ja061203b.
3
Synthesis of furano[2,3-c]pyran-3-one and thieno[2,3-c]pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes: total synthesis of a Baccharis-derived cadinene derivative.
J Org Chem. 2002 Jun 14;67(12):4177-85. doi: 10.1021/jo011136y.
4
Platinum-catalyzed cycloisomerization reactions of enynes.
J Am Chem Soc. 2001 Dec 5;123(48):11863-9. doi: 10.1021/ja0109343.
5
Computational support for tunneling in thermal[1,7]-hydrogen shift reactions.
J Org Chem. 2001 Aug 24;66(17):5897-900. doi: 10.1021/jo010622i.
6
Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives.
Org Lett. 2000 May 4;2(9):1267-9. doi: 10.1021/ol005691i.
Zotero 插件