Ynones in Reflex-Michael Addition, CuAAC, and Cycloaddition, as Well as their Use as Nucleophilic Enols, Electrophilic Ketones, and Allenic Precursors

被引：24

作者：

Wang, Zhan-Yong ^{[1
]}

Wang, Kai-Kai ^{[1
]}

Chen, Rongxiang ^{[1
]}

Liu, Huan ^{[1
]}

Chen, Kaijun ^{[2
]}

机构：

[1] Xinxiang Univ, Coll Chem & Chem Engn, Xinxiang 453000, Henan, Peoples R China

[2] Lishui Univ, Dept Chem, 1 Xueyuan Rd, Lishui 323000, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Tandem reactions; Michael addition; Enols; Terminal alkynes; Ynones; DIELS-ALDER REACTION; CARBON SIGMA-BONDS; TANDEM CYCLIZATION; ALKYNYL KETONES; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE CYCLIZATION; DICTYODENDRINS B; FACILE SYNTHESIS; SULFINIC ACIDS;

D O I：

10.1002/ejoc.201901921

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The great success of ynones in synthesis is rooted in their multiple functional groups. Herein, reactions triggered by the reflex-Michael addition, ynones in copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), and formal cycloaddition as well as the use of ynones as nucleophilic enols, electrophilic ketones, and allenic precursors were thoroughly discussed and summarized. Multi-component reactions, rearrangements, cycloadditions, regio- and stereoselective synthesis, coupling, and cycloaddition are depicted in detail. This review focused on advances of ynones chemistry in the last decade (2009-2019). We hope it will promote future research in this area.

引用

页码：2456 / 2474

页数：19

共 135 条

[1] Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles [J].

Abbiati, Giorgio ;

Arcadi, Antonio ;

Marinelli, Fabio ;

Rossi, Elisabetta .

SYNTHESIS-STUTTGART, 2014, 46 (06) :687-721

[2] Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization) [J].

Alcaide, Benito ;

Almendros, Pedro ;

Lazaro-Milla, Carlos ;

Delgado-Martinez, Patricia .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (32) :8186-8194

[3] Phosphine catalysed (5+1) annulation of ynone/cinnamates with primary amines [J].

Ametovski, Jhi ;

Dutta, Uttam ;

Burchill, Laura ;

Maiti, Debabrata ;

Lupton, David W. ;

Hooper, Joel F. .

CHEMICAL COMMUNICATIONS, 2017, 53 (97) :13071-13074

[4]

[Anonymous], 2013, ANGEW CHE

[5]

[Anonymous], 2015, ANGEW CHEM, V127, P6682

[6] Nickel-catalyzed multicomponent coupling reaction using ynones [J].

Arai, Takayoshi ;

Ikematsu, Yui ;

Suemitsu, Yuuki .

PURE AND APPLIED CHEMISTRY, 2010, 82 (07) :1485-1490

[7]

Axelrod A., 2013, ANGEW CHEM, V125, P3505

[8] Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration [J].

Axelrod, Abram ;

Eliasen, Anders M. ;

Chin, Matthew R. ;

Zlotkowski, Katherine ;

Siegel, Dionicio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) :3421-3424

[9] Intramolecular Didehydro-Diels-Alder Reaction for the Synthesis of Benzo-and Dihydrobenzo-Fused Heterocycles [J].

Bober, Ashley E. ;

Proto, Justin T. ;

Brummond, Kay M. .

ORGANIC LETTERS, 2017, 19 (07) :1500-1503

[10] Intramolecular Didehydro-Diels-Alder Reaction and Its Impact on the Structure-Function Properties of Environmentally Sensitive Fluorophores [J].

Brummond, Kay M. ;

Kocsis, Laura S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (08) :2320-2329

← 1 2 3 4 5 6 7 8 9 10 →