Literature DB >> 12175197

Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones.

Yong Huang1, Viresh H Rawal.   

Abstract

We report the first examples of hydrogen-bond-promoted acceleration of hetero-Diels-Alder reactions and the use of such catalysis for the hetero-Diels-Alder reactions of simple, unactivated ketones. Several spiro-fused dihydropyans were synthesized in good yields using this procedure. This activation protocol represents an attractive and operationally simple alternative to conventional, Lewis acid catalysis.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 12175197     DOI： 10.1021/ja0267627

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

1.  Reverse-docking study of the TADDOL-catalyzed asymmetric hetero-Diels-Alder reaction.

Authors:  D Joseph Harriman; Ghislain Deslongchamps
Journal:  J Mol Model       Date:  2006-02-23       Impact factor: 1.810

Review 2.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

3.  Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.

Authors:  David L Sloman; Branko Mitasev; Stephen S Scully; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-18       Impact factor: 15.336

4.  Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

Authors:  Ruth Gordillo; Travis Dudding; Christopher D Anderson; K N Houk
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

5.  Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-09-14       Impact factor: 15.419

6.  Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives.

Authors:  Zhuo Tang; Fan Jiang; Xin Cui; Liu-Zhu Gong; Ai-Qiao Mi; Yao-Zhong Jiang; Yun-Dong Wu
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-12       Impact factor: 11.205

7.  Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding.

Authors:  Avinash N Thadani; Ana R Stankovic; Viresh H Rawal
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

8.  Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates.

Authors:  Michael P Doyle; Marcela Valenzuela; Penglin Huang
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-01       Impact factor: 11.205

9.  A redox economical synthesis of bioactive 6,12-guaianolides.

Authors:  Bo Wen; Joseph K Hexum; John C Widen; Daniel A Harki; Kay M Brummond
Journal:  Org Lett       Date:  2013-05-10       Impact factor: 6.005

10.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.