Zirconocene-assisted remote cleavage of C-C and C-O bonds: application to acyclic stereodefined metalated hydrocarbons

被引:15
作者
Bruffaerts, J.
Pierrot, D.
Marek, I. [1 ]
机构
[1] Technion Israel Inst Technol, Schulich Fac Chem, Mallat Family Lab Organ Chem, IL-32000 Haifa, Israel
基金
欧洲研究理事会;
关键词
CATALYZED ASYMMETRIC ISOMERIZATION; QUATERNARY STEREOGENIC CENTERS; HECK ARYLATIONS; FUNCTIONALIZATION; DERIVATIVES; ALKENES; DIENES; ALKYLIDENECYCLOPROPANES; COMPLEXES; STRATEGY;
D O I
10.1039/c6ob01910b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The molding of molecules through remote functionalisation has increasingly become popular as it provides original and flexible synthetic alternatives to classical retrosynthetic analysis. In this Perspective article, we summarise more than a decade of studies in the specific field of remote activation of inert C-C and C-O bonds using the unique abilities of organozirconocene species mainly from our own research group. By demonstrating that these reactions represent novel and powerful entries towards acyclic stereodefined reactive organometallic species, we aim to show the vast opportunities this concept-driven methodology discovery offers.
引用
收藏
页码:10325 / 10330
页数:6
相关论文
共 59 条
[21]   Aminocatalytic remote functionalization strategies [J].
Jiang, Hao ;
Albrecht, Lukasz ;
Jorgensen, Karl Anker .
CHEMICAL SCIENCE, 2013, 4 (06) :2287-2300
[22]   Iridium-Catalyzed Selective Isomerization of Primary Allylic Alcohols [J].
Li, Houhua ;
Mazet, Clement .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (06) :1232-1241
[23]   Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds [J].
Lin, Luqing ;
Romano, Ciro ;
Mazet, Clement .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (32) :10344-10350
[24]   Improved Catalysts for the Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols Based on Charton Analysis [J].
Mantilli, Luca ;
Gerard, David ;
Torche, Sonya ;
Besnard, Celine ;
Mazet, Clement .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) :12736-12745
[25]   Expanded scope for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols using readily accessible second-generation catalysts [J].
Mantilli, Luca ;
Mazet, Clement .
CHEMICAL COMMUNICATIONS, 2010, 46 (03) :445-447
[26]   Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols [J].
Mantilli, Luca ;
Gerard, David ;
Torche, Sonya ;
Besnard, Celine ;
Mazet, Clement .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5143-5147
[27]  
Marek I., 2006, SYNLETT, P501
[28]   Selective Carbon-Carbon Bond Cleavage for the Stereoselective Synthesis of Acyclic Systems [J].
Marek, Ilan ;
Masarwa, Ahmad ;
Delaye, Pierre-Olivier ;
Leibeling, Markus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) :414-429
[29]   All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C-C Bonds per Chemical Step [J].
Marek, Ilan ;
Minko, Yury ;
Pasco, Morgane ;
Mejuch, Tom ;
Gilboa, Noga ;
Chechik, Helena ;
Das, Jaya P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (07) :2682-2694
[30]  
Marek I, 2005, HANDBOOK OF FUNCTIONALIZED ORGANOMETALLICS: APPLICATIONS IN SYNTHESIS, P503