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Tetrahedron. 2007 Apr 2;63(14):2959-2965. doi: 10.1016/j.tet.2007.01.046.
2
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[The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds].[周环反应的化学及其在杂环化合物合成中的应用]
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Electronic Control of Product Distribution in the [5+5]-Coupling of ortho-Alkynylbenzaldehyde Derivatives and γ,δ-Unsaturated Carbene Complexes.邻炔基苯甲醛衍生物与γ,δ-不饱和卡宾配合物[5+5]偶联中产物分布的电子控制
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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.以γ,δ-不饱和卡宾配合物与2-炔基苯基酮的净[5+5]环加成反应为关键步骤全合成安托非尼。
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.通过[1,7]-氢迁移实现1-取代的3,5-二烯-1-炔的热催化和金属催化环化：3-烯-1-炔-5-醛单元与环酮之间串联羟醛缩合-脱水和芳构化催化反应的进展
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.通过3-炔基-2-杂芳族甲醛与费歇尔卡宾配合物的偶联合成呋喃并[2,3-c]吡喃-3-酮和噻吩并[2,3-c]吡喃-3-酮衍生物：一种源自巴卡里斯属植物的杜松烯衍生物的全合成
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.热[1,7]-氢迁移反应中隧穿效应的计算支持
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.费歇尔卡宾配合物与邻炔基苯甲酰衍生物偶联反应中形成的异苯并呋喃中间体的生成与捕获
Org Lett. 2000 May 4;2(9):1267-9. doi: 10.1021/ol005691i.

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.

DOI:10.1016/j.tet.2007.01.046
PMID:18382602
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1868474/
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。