Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

被引:51
作者
Soengas, Raquel G. [1 ]
Rodriguez-Solla, Humberto [1 ]
机构
[1] Univ Oviedo, Dept Organ & Inorgan Chem, Julian Claveria 6, Oviedo 33006, Spain
关键词
1; 3-dienes; dienylation; cross-coupling; olefin metathesis; PALLADIUM; ISOMERIZATION; BROMIDES; ALKYNES; RHODIUM;
D O I
10.3390/molecules26020249
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.
引用
收藏
页数:40
相关论文
共 50 条
[21]   Palladium-Catalyzed Elimination/Isomerization of Enol Triflates into 1,3-Dienes [J].
Crouch, Ian T. ;
Dreier, Timothy ;
Frantz, Doug E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6128-6132
[22]   Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes [J].
Choudhury, Partha P. ;
Welker, Mark E. .
MOLECULES, 2015, 20 (09) :16892-16907
[23]   Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides [J].
Li, Ming-Ming ;
Cheng, Lei ;
Xiao, Li-Jun ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) :2948-2951
[24]   A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-Dienes [J].
Fiorito, Daniele ;
Folliet, Sarah ;
Liu, Yangbin ;
Mazet, Clement .
ACS CATALYSIS, 2018, 8 (02) :1392-1398
[25]   Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System [J].
Al-Jawaheri, Yassir ;
Turner, Matthew ;
Kimber, Marc C. .
SYNTHESIS-STUTTGART, 2018, 50 (12) :2329-2336
[26]   Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes [J].
Shen, Hong-Cheng ;
Wu, Yu-Feng ;
Zhang, Ying ;
Fan, Lian-Feng ;
Han, Zhi-Yong ;
Gong, Liu-Zhu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) :2372-2376
[27]   Nickel-catalyzed hydrobivinylation of enones with 1,3-dienes [J].
Li, Ying ;
Zhang, Wei-Song ;
Sun, Shao-Han ;
Mei, Yong-Kang ;
Ji, Ding-Wei ;
Hu, Yan-Cheng ;
Chen, Qing-An .
CELL REPORTS PHYSICAL SCIENCE, 2023, 4 (10)
[28]   Boron-Catalyzed Hydroarylation of 1,3-Dienes with Arylamines [J].
Kumar, Gautam ;
Qu, Zheng-Wang ;
Grimme, Stefan ;
Chatterjee, Indranil .
ORGANIC LETTERS, 2021, 23 (22) :8952-8957
[29]   Recent advances on catalytic asymmetric difunctionalization of 1,3-dienes [J].
Xiong, Yang ;
Sun, Youwen ;
Zhang, Guozhu .
TETRAHEDRON LETTERS, 2018, 59 (04) :347-355
[30]   A novel stereoselective synthesis of symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes [J].
Babudri, Francesco ;
Farinola, Gianluca M. ;
Naso, Francesco ;
Ragni, Roberta ;
Spina, Giulia .
SYNTHESIS-STUTTGART, 2007, (19) :3088-3092