Literature DB >> 21265565

Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Andrew DeAngelis1, Valerie W Shurtleff, Olga Dmitrenko, Joseph M Fox.   

Abstract

A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh(2)(S-NTTL)(4), the putative Rh-carbene intermediates from α-alkyl-α-diazoesters react with indoles at C(3) to provide α-alkyl-α-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21265565      PMCID： PMC3144986          DOI： 10.1021/ja1093309

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


  31 in total

1.  First X-ray structure of a N-naphthaloyl-tethered chiral dirhodium(II) complex: structural basis for tether substitution improving asymmetric control in olefin cyclopropanation.

Authors:  Ashraf Ghanem; Michael G Gardiner; Rachel M Williamson; Paul Müller
Journal:  Chemistry       Date:  2010-03-15       Impact factor: 5.236

2.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

Review 3.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

Review 4.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

5.  Rh-catalyzed intermolecular reactions of alkynes with alpha-diazoesters that possess beta-hydrogens: ligand-based control over divergent pathways.

Authors:  Patricia Panne; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

6.  Rhodium-catalyzed [3 + 2] annulation of indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

7.  Enantioselective oxidative cross-coupling reaction of 3-indolylmethyl C-H bonds with 1,3-dicarbonyls using a chiral Lewis acid-bonded nucleophile to control stereochemistry.

Authors:  Chang Guo; Jin Song; Shi-Wei Luo; Liu-Zhu Gong
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

8.  Rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids.

Authors:  Takahiro Nishimura; Sho Hirabayashi; Yuichi Yasuhara; Tamio Hayashi
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

9.  Convenient preparation of indolyl Malonates via Carbenoid insertion.

Authors:  Romelo Gibe; Michael A Kerr
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

10.  Rh-catalyzed formation of dioxolanes from alpha-alkyl diazoesters: diastereoselective cycloadditions of carbonyl ylides with selectivity over beta-hydride elimination.

Authors:  Andrew DeAngelis; Patricia Panne; Glenn P A Yap; Joseph M Fox
Journal:  J Org Chem       Date:  2008-01-12       Impact factor: 4.354
View more
  15 in total

1.  Highly enantioselective trapping of zwitterionic intermediates by imines.

Authors:  Huang Qiu; Ming Li; Li-Qin Jiang; Feng-Ping Lv; Li Zan; Chang-Wei Zhai; Michael P Doyle; Wen-Hao Hu
Journal:  Nat Chem       Date:  2012-07-29       Impact factor: 24.427

2.  Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Jamal A Malik; Mikhail Zibinsky; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2011-06-20       Impact factor: 15.419

3.  Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration.

Authors:  Andrew DeAngelis; Robert Panish; Joseph M Fox
Journal:  Acc Chem Res       Date:  2015-12-21       Impact factor: 22.384

4.  Rh2(S-biTISP)2-catalyzed asymmetric functionalization of indoles and pyrroles with vinylcarbenoids.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2012-03-27       Impact factor: 6.005

5.  Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration.

Authors:  Andrew DeAngelis; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2012-06-19       Impact factor: 15.419

6.  Regioselective Arene C-H Alkylation Enabled by Organic Photoredox Catalysis.

Authors:  Natalie Holmberg-Douglas; Nicholas P R Onuska; David A Nicewicz
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-17       Impact factor: 15.336

7.  Myoglobin-Catalyzed C-H Functionalization of Unprotected Indoles.

Authors:  David A Vargas; Antonio Tinoco; Vikas Tyagi; Rudi Fasan
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-06       Impact factor: 15.336

8.  Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters.

Authors:  David T Boruta; Olga Dmitrenko; Glenn P A Yap; Joseph M Fox
Journal:  Chem Sci       Date:  2012-05       Impact factor: 9.825

9.  Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.

Authors:  Robert Panish; Ramajeyam Selvaraj; Joseph M Fox
Journal:  Org Lett       Date:  2015-08-04       Impact factor: 6.005

10.  Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition.

Authors:  Robert Panish; Srinivasa R Chintala; David T Boruta; Yinzhi Fang; Michael T Taylor; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.