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

[21] Synthesis of 1,2-bisalkylidenecyclopentanes from 1,6-allenynes via stereoselective addition of nucleophiles to ruthenacyclopentenes
Saito, Nozomi
Kohyama, Yuh
Tanaka, Yuki
Sato, Yoshihiro
CHEMICAL COMMUNICATIONS, 2012, 48 (31) : 3754 - 3756
[22] Cobalt-catalyzed Alder-ene reaction
Hilt, Gerhard
Treutwein, Jonas
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) : 8500 - 8502
[23] Phosphazene-triazine polymers by alder-ene reaction
Nair, CPR
Ninan, KN
POLYMERS & POLYMER COMPOSITES, 2004, 12 (01): : 55 - 62
[24] Cyclomatrix phosphazene polymers via Alder-ene reactions
Nair, CPR
Sunitha, M
Ninan, KN
POLYMERS & POLYMER COMPOSITES, 2002, 10 (06): : 457 - 465
[25] Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction
Cheong, Paul Ha-Yeon
Morganelli, Philip
Luzung, Michael R.
Houk, K. N.
Toste, F. Dean
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) : 4517 - 4526
[26] Rh(III)-catalyzed hydrative cyclization of 1,6-allenynes: synthesis of six-membered nitrogen and oxygen heterocycles
Quan, Shasha
Wang, Yuanyuan
Zheng, Kewen
Tong, Xiaofeng
TETRAHEDRON LETTERS, 2015, 56 (01) : 215 - 217
[27] Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Ene-ynamides
Nishimura, Takahiro
Takiguchi, Yuka
Maeda, Yuko
Hayashi, Tamio
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1374 - 1382
[28] Rhodium(I)-catalyzed Alder-ene reactions of allenic ynones
Painter, Thomas O., Jr.
Brummond, Kay M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3257 - U3258
[29] Alder-ene reaction: Aromaticity and activation-strain analysis
Fernandez, Israel
Bickelhaupt, F. Matthias
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2012, 33 (05) : 509 - 516
[30] Reactivity and Selectivity in the Intermolecular Alder-Ene Reactions of Arynes with Functionalized Alkenes
Gupta, Saswata
Xie, Peipei
Xia, Yuanzhi
Lee, Daesung
ORGANIC LETTERS, 2017, 19 (19) : 5162 - 5165

← 1 2 3 4 5 →