Gold-Catalyzed Cycloadditions Involving Allenes: Mechanistic Insights from Theoretical Studies

被引：31

作者：

Montserrat, Sergi ^{[1
]}

Ujaque, Gregori ^{[1
]}

Lopez, Fernando ^{[2
]}

Mascarenas, Jose L. ^{[3
]}

Lledos, Agusti ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[3] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

COMPUTATIONAL MECHANISMS OF AU AND PT CATALYZED REACTIONS | 2011年 / 302卷

关键词：

Allene; Cycloaddition; DFT studies; Gold catalysis; Reaction mechanisms; CYCLOISOMERIZATION; PLATINUM; CARBENE; REARRANGEMENT; CHEMISTRY; 4C+3C; 1,5-ALLENYNES; ALLENEDIENES; CYCLIZATION; ACTIVATION;

D O I：

10.1007/128_2010_121

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Allenes, owing to their special structural characteristics related to the presence of two pi bonds in a formally strained manner, are particularly prone to undergo gold-activated reactions, particularly cycloaddition processes. Theoretical studies based on DFT calculations have been very useful to explain observed reactivities and advance mechanistic proposals.

引用

页码：225 / 248

页数：24

共 50 条

[21] Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes
Campeau, Dominic
Rayo, David F. Leon
Mansour, Ali
Muratov, Karim
Gagosz, Fabien
CHEMICAL REVIEWS, 2021, 121 (14) : 8756 - 8867
[22] Gold-Catalyzed Intermolecular Markovnikov Hydroamination of Allenes with Secondary Amines
Zeng, Xiaoming
Soleilhavoup, Michele
Bertrand, Guy
ORGANIC LETTERS, 2009, 11 (15) : 3166 - 3169
[23] Gold-catalyzed intramolecular hydroamination of allenes: a case of chirality transfer
Patil, Nitin T.
Lutete, Leopold Mpaka
Nishina, Naoko
Yamamoto, Yoshinori
TETRAHEDRON LETTERS, 2006, 47 (27) : 4749 - 4751
[24] Gold-catalyzed highly enantioselective synthesis of axially chiral allenes
Lo, Vanessa Kar-Yan
Wong, Man-Kin
Che, Chi-Ming
ORGANIC LETTERS, 2008, 10 (03) : 517 - 519
[25] An easy access to chromanes via the gold-catalyzed hydroarylation of allenes
Fazeli, Azadeh
Pflaesterer, Daniel
Rudolph, Matthias
Hashmi, A. Stephen K.
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 795 : 68 - 70
[26] Mechanistic insights into nickel- and gold-catalyzed diastereoselective [4+2+1] cycloadditions between dienynes and diazo compounds: a DFT study
Lv, Kang
Bao, Xiaoguang
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (03): : 693 - 702
[27] Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: Ligand-controlled regioselectivity
Xia, Yuanzhi
Dudnik, Alexander S.
Gevorgyan, Vladimir
Li, Yahong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) : 6940 - +
[28] Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: Ligand-controlled regioselectivity
Xia, Yuanzhi
Dudnik, Alexander S.
Gevorgyan, Vladimir
Li, Yahong
Journal of the American Chemical Society, 2008, 130 (22): : 6940 - 6941
[29] Gold-catalyzed cycloisomerization of α-aminoallenes to 3-pyrrolines optimization and mechanistic studies
Morita, Nobuyoshi
Krause, Norbert
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (20) : 4634 - 4641
[30] Meeting the Challenge of Intermolecular Gold(I)-Catalyzed Cycloadditions of Alkynes and Allenes
Muratore, Michael E.
Homs, Anna
Obradors, Carla
Echavarren, Antonio M.
CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (11) : 3066 - 3082

← 1 2 3 4 5 →