Literature DB >> 19173649

Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes.

K C Nicolaou1, Rüdiger Reingruber, David Sarlah, Stefan Bräse.   

Abstract

Enantioselective organo-SOMO catalysis has, in the last two years, been the subject of considerable development and exploration. A number of new and unique transformations have been reported, such as alpha-allylation, alpha-oxyamination, alpha-enolation, and alpha-vinylation of aldehydes. Herein, we report a modification of this activation mode that involves the intramolecular Friedel-Crafts-type alpha-arylation of aldehydes carrying electron-donating groups on their aromatic nucleus and its application to the total synthesis of demethyl calamenene, a potent cytotoxic agent against human adenocarcinoma A 549.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19173649     DOI： 10.1021/ja809405c

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


  14 in total

Review 1.  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

2.  Enantioselective organo-SOMO cascade cycloadditions: a rapid approach to molecular complexity from simple aldehydes and olefins.

Authors:  Nathan T Jui; Esther C Y Lee; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

3.  Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

Authors:  Wei Liu; Siraj Z Ali; Stephen E Ammann; M Christina White
Journal:  J Am Chem Soc       Date:  2018-08-17       Impact factor: 15.419

4.  Nature of intermediates in organo-SOMO catalysis of alpha-arylation of aldehydes.

Authors:  Joann M Um; Osvaldo Gutierrez; Franziska Schoenebeck; K N Houk; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

5.  Mechanistic complexity in organo-SOMO activation.

Authors:  James J Devery; Jay C Conrad; David W C MacMillan; Robert A Flowers
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

6.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

Authors:  Scott E Denmark; Alex Jaunet
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

7.  Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations.

Authors:  Sofia Vasilakaki; Efrosini Barbayianni; Georgios Leonis; Manthos G Papadopoulos; Thomas Mavromoustakos; Michael H Gelb; George Kokotos
Journal:  Bioorg Med Chem       Date:  2016-03-02       Impact factor: 3.641

8.  Enantioselective alpha-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway.

Authors:  Jay C Conrad; Jongrock Kong; Brian N Laforteza; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

9.  Enantioselective Total Synthesis of Antibiotic CJ-16,264, Synthesis and Biological Evaluation of Designed Analogues, and Discovery of Highly Potent and Simpler Antibacterial Agents.

Authors:  K C Nicolaou; Kiran Kumar Pulukuri; Stephan Rigol; Marek Buchman; Akshay A Shah; Nicholas Cen; Megan D McCurry; Kathryn Beabout; Yousif Shamoo
Journal:  J Am Chem Soc       Date:  2017-10-24       Impact factor: 15.419

10.  The Intramolecular Asymmetric Allylation of Aldehydes via Organo-SOMO Catalysis: A Novel Approach to Ring Construction.

Authors:  Phong V Pham; Kate Ashton; David W C Macmillan
Journal:  Chem Sci       Date:  2011-05-19       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.