A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

被引：6

作者：

Joyce, Liam M. ^{[1
]}

Drew, Melanie A. ^{[1
]}

Tague, Andrew J. ^{[1
]}

Thaima, Thanaphat ^{[1
]}

Gouranourimi, Ali ^{[2
]}

Ariafard, Alireza ^{[2
]}

Pyne, Stephen G. ^{[1
]}

Hyland, Christopher J. T. ^{[1
]}

机构：

[1] Univ Wollongong, Sch Chem & Biomol Sci, Mol Horizons Res Inst, Wollongong, NSW 2522, Australia

[2] Univ Tasmania, Sch Phys Sci, Hobart, Tas 7018, Australia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 12期

基金：

澳大利亚研究理事会;

关键词：

1; 6-allenyne; Alder-ene; cycloisomerization; lactam; computations; INTRAMOLECULAR 2+2 CYCLOADDITION; GOLD-CATALYZED CYCLOISOMERIZATION; ALLENE; CYCLIZATION; ACTIVATION; CONSTRUCTION; SUBSTITUENT; LACTONES; NITROGEN;

D O I：

10.1002/chem.202104022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermally induced cycloisomerization reactions of 1,6-allenynes gives alpha-methylene-gamma-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

引用

页数：5

共 50 条

[41] Long distance unconjugated agostic-assisted 1,5-H shift in a Ru-mediated Alder-ene type reaction: mechanism and stereoselectivity
Shan, Chunhui
Zhong, Kangbao
Qi, Xiaotian
Xu, Dongdong
Qu, Ling-Bo
Bai, Ruopeng
Lan, Yu
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (21): : 3178 - 3185
[42] An Electrophilic Ruthenium Complex that Enables the Cycloisomerization of 1,6-Enynes to Access Azabicyclo[4.1.0]heptenes
Liu, Rui
Yang, Dongfeng
Chang, Fengwei
Giordano, Laurent
Liu, Guohua
Tenaglia, Alphonse
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (11) : 2011 - 2016
[43] Ruthenium-Catalyzed Cycloisomerization of 1,6-Diynes with Styryl Terminals Leading to Indenylidene Cycloalkanes
Yamamoto, Yoshihiko
Nishimura, Kei-ichiro
Shibuya, Masatoshi
ACS CATALYSIS, 2017, 7 (02): : 1101 - 1107
[44] Enantioselective Rhodium-Catalyzed Cycloisomerization of (E)-1,6-Enynes
Deng, Xu
Ni, Shao-Fei
Han, Zheng-Yu
Guan, Yu-Qing
Lv, Hui
Dang, Li
Zhang, Xu-Mu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (21) : 6295 - 6299
[45] Unexpected Pd-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Alder-Ene Reaction: Facile Synthesis of Some Not Readily Available 2,3-Dihydrofuran Derivatives
Shen, Ruwei
Zhu, Shugao
Huang, Xian
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) : 4118 - 4123
[46] Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes
Zriba, Riadh
Gandon, Vincent
Aubert, Corinne
Fensterbank, Louis
Malacria, Max
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (05) : 1482 - 1491
[47] Propargylic Dialkyl Effect for Cyclobutene Formation through Ir(III)-Catalyzed Cycloisomerization of 1,6-Enynes
Zhu, Xuanyu
Li, Yi
Luo, Hongtao
Li, Jing
Hua, Yuhui
Liu, Guohua
Li, Lingling
Liu, Rui
ORGANIC LETTERS, 2024, 26 (04) : 966 - 970
[48] Gold-Catalyzed Sequential Cycloisomerization of 1,3,9-Ene-allene-ynes to Fused Spirocarbocycles
Chen, Xianxiao
Ling, Xiangxiang
An, Di
Rao, Weidong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (32) : 5227 - 5233
[49] Ruthenium-Catalyzed Regioselective Tandem Cycloisomerization/Diels-Alder Reaction of 1,7-Enynes
Logeswaran, Ravichandran
Jeganmohan, Masilamani
ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (02)
[50] Comparison of homogeneous and heterogeneous Ga(III) catalysis in the cycloisomerization of 1,6-enynes
Hassen, Khadija Ben Hadj
Gaubert, Kevin
Vaultier, Michel
Pucheault, Mathieu
Antoniotti, Sylvain
GREEN CHEMISTRY LETTERS AND REVIEWS, 2014, 7 (03) : 243 - 249

← 1 2 3 4 5 →