Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents

被引：118

作者：

Reyes-Rodriguez, Gabriel J. ^{[1
]}

Rezayee, Nomaan M. ^{[1
]}

Vidal-Albalat, Andreu ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

CHEMICAL REVIEWS | 2019年 / 119卷 / 06期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; ORGANOCATALYTIC MICHAEL ADDITION; ASYMMETRIC TOTAL-SYNTHESIS; DIHYDROCINNAMIC ACID-DERIVATIVES; OXIDATIVE COUPLING REACTION; DIVERGENT TOTAL SYNTHESES; HIGH-YIELDING SYNTHESIS; CONCISE TOTAL-SYNTHESIS; ANTI-TUMOR ANTIBIOTICS; FORMAL TOTAL-SYNTHESIS;

D O I：

10.1021/acs.chemrev.8b00583

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diarylprolinol silyl ethers are among the most utilized stereoselective organocatalysts for the construction of complex molecules. With their debut in 2005, these catalysts have been applied in numerous method developments primarily leveraging enamine and iminium-ion catalysis. These strategies have extended into the preparation of complex molecules in both academic and industrial settings. This Review intends to give an overview of the application of the diarylprolinol silyl ether catalysts in total synthesis. Furthermore, integration of these catalysts in patent literature is also disclosed highlighting the versatility of the catalytic system.

引用

页码：4221 / 4260

页数：40

共 303 条

[1] The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu®):: A challenge for synthesis & process research [J].

Abrecht, S ;

Harrington, P ;

Iding, H ;

Karpf, M ;

Trussardi, R ;

Wirz, B ;

Zutter, U .

CHIMIA, 2004, 58 (09) :621-629

[2] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[3] Catalytic Enantioselective β-Alkylation of α,β-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes [J].

Afewerki, Samson ;

Breistein, Palle ;

Pirttila, Kristian ;

Deiana, Luca ;

Dziedzic, Pawel ;

Ibrahem, Ismail ;

Cordova, Armando .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (32) :8784-8788

[4] A Simple Recipe for Sophisticated Cocktails: Organocatalytic One-Pot Reactions-Concept, Nomenclature, and Future Perspectives [J].

Albrecht, Lukasz ;

Jiang, Hao ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8492-8509

[5] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[6] Exploring the Boundaries of "Practical": De Novo Syntheses of Complex Natural Product-Based Drug Candidates [J].

Allred, Tyler K. ;

Manoni, Francesco ;

Harran, Patrick G. .

CHEMICAL REVIEWS, 2017, 117 (18) :11994-12051

[7] Penicillium expansum:: Consistent production of patulin, chaetoglobosins, and other secondary metabolites in culture and their natural occurrence in fruit products [J].

Andersen, B ;

Smedsgaard, J ;

Frisvad, JC .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (08) :2421-2428

[8] Lignopurines: A new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation [J].

Angeles Castro, Ma ;

Ma Miguel del Corral, Jose ;

Garcia, Pablo A. ;

Victoria Rojo, Ma ;

Bento, Ana C. ;

Mollinedo, Faustino ;

Francesch, Andres M. ;

San Feliciano, Arturo .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 58 :377-389

[9] Synthesis and Biological Evaluation of New Podophyllic Aldehyde Derivatives with Cytotoxic and Apoptosis-Inducing Activities [J].

Angeles Castro, Ma ;

Miguel del Corral, Jose Ma ;

Garcia, Pablo A. ;

Victoria Rojo, Ma ;

de la Iglesia-Vicente, Janis ;

Mollinedo, Faustino ;

Cuevas, Carmen ;

San Feliciano, Arturo .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (03) :983-993

[10]

[Anonymous], 2014, IUPAC Compendium of Chemical Terminology (The "Gold Book")

← 1 2 3 4 5 6 7 8 9 10 →