在21世纪，绿色有机化学越来越受到科学家们的关注，这也对有机合成的发展提出了更高的要求。在追求和探索“绿色有机化学”的研究过程中，新型催化剂的应用一直是其中一个非常重要的环节。近年来的研究发现，金催化剂（主要是Au(I)配合物）可以广泛应用于催化各种类型的1，n-烯炔的环化反应。其中，在金催化1，6-烯炔的环化反应过程中，会发生各种异构化反应，生成多种异构的多环产物，所以反应性质最为丰富，应用最广泛。这一类金催化反应的催化活性高、反应选择性好，原子利用率高，符合“绿色化学”的理念，可以用于构建含有或不含杂原子的多环化合物，同时，添加手性配体，还可以合成手性碳环或杂环化合物。

  本文将简单介绍金催化1，n-烯炔类化合物的各种环化反应，重点讨论1，6-烯炔环异构化反应，同时，对1，6-烯炔与羰基的环异构加成反应进行简单介绍。由于多元环结构是许多天然有机活性物质的重要组成部分，因此，通过金催化反应，从1，n-烯炔结构出发，构建多环化合物的研究具有重要的意义。

  Green organic chemistry is getting more and more attention in the 21st century, which also put forward higher requirements for the development of organic synthesis. In the process of pursuing and exploring "green organic chemistry", the development of new catalysts and their application has always been an important research topic. Recent studies have found that gold catalysts (mainly Au (I) complexes) can be widely used to catalyze 1, n-enyne’s cyclization reaction. Among these reactions, high catalytic activity, good selectivity and high atom utilization could be observed, which is in line with the concept of "green chemistry" and can be utilized to construct poly- heterocyclic or carbocyclic compounds.

  This thesis will briefly introduce gold-catalyzed cyclization reactions of 1, n-enyne, focusing on 1,6-enyne’s cycloisomerization reaction. In addition, the coupling reaction of 1,6-enyne with carbonyl containing molecule, either through intramolecular or intermolecular process, were also discussed.        Considering the importance of polycyclic ring in many natural bioactive compounds, it is of great significance to develop new method for the synthesis of polycyclic structure from the gold-catalyzed 1, n-enyne cyclization reaction.

[1] 陈翠丽. 金催化烯炔类串联环化反应研究[D].南京林业大学,2018.

[2] Ito Y, Sawamura M, Hayashi T. Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex[J]. Journal of the American Chemical Society, 1987, 18(6): 6405-6406.

[3] 张舒尧. 金催化的串联反应于杂环化合物的合成[D].山东大学,2017.

[4] 郭佳,王岩石,程卯生,刘永祥.金催化炔烃的碳碳键形成在天然产物全合成中的应用[J].中国药物化学杂志,2014,24(01):59-69.

[5] Trost B M，Lautens M. J. Am. Chem. Soc. ，1985，107:1781 —1783

[6] 陈茂,翁玥,雷爱文.过渡金属催化的1,n-烯炔类化合物的不对称环异构化反应[J].化学进展,2010,22(07):1341-1352.

[7] 童晓峰,张兆国.过渡金属催化的1,6-烯炔环异构化反应[J].有机化学,2004(06):591-599+571.

[8] Zhang Liming,Wang Shaozhong. Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction.[J]. Journal of the American Chemical Society,2006,128(5).

[9] Shi Xiao dong,Gorin David J,Toste F Dean. Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement.[J]. Journal of the American Chemical Society,2005,127(16).

[10] Luzung Michael R,Markham Jordan P,Toste F Dean. Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes.[J]. Journal of the American Chemical Society,2004,126(35).

[11] Jiménez-Nú?ez Eloísa,Claverie Christelle K,Nieto-Oberhuber Cristina,Echavarren Antonio M. Prins cyclizations in Au-catalyzed reactions of enynes.[J]. Angewandte Chemie (International ed. in English),2006,45(33).

[12] Schelwies Mathias,Dempwolff Adrian L,Rominger Frank,Helmchen Günter. Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes.[J]. Angewandte Chemie (International ed. in English),2007,46(29).

[13] Schelwies Mathias,Moser Ralph,Dempwolff Adrian L,Rominger Frank,Helmchen Günter. Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes: reactivity, scope, and mechanistic aspects.[J]. Chemistry (Weinheim an der Bergstrasse, Germany),2009,15(41).

[14] Escribano-Cuesta Ana,López-Carrillo Verónica,Janssen Dominic,Echavarren Antonio M. Gold-catalyzed reactions of 1,5- and 1,6-enynes with carbonyl compounds: cycloaddition vs. metathesis.[J]. Chemistry (Weinheim an der Bergstrasse, Germany),2009,15(23).

[15] Matsuda Takanori,Sakurai Yusuke. Gold(I)-catalyzed ring-expanding spiroannulation of cyclopropenones with enynes.[J]. The Journal of organic chemistry,2014,79(6).

[16] Dorel Ruth,Echavarren Antonio M. Gold-Catalyzed Reactions via Cyclopropyl Gold Carbene-like Intermediates.[J]. The Journal of organic chemistry,2015,80(15).

[17] 马骏. 基于炔烃为卡宾前体的反应方法学研究[D].华南理工大学,2017.

[18] 肖晔林.金催化炔醛与烯烃的Diels Alder环化反应[J].现代工业经济和信息化,2018,8(18):132-133.

[19] Gawade Sagar Ashok,Bhunia Sabyasachi,Liu Rai-Shung. Intermolecular gold-catalyzed diastereo- and enantioselective [2+2+3] cycloadditions of 1,6-enynes with nitrones.[J]. Angewandte Chemie (International ed. in English),2012,51(31).