Literature DB >> 18558761

Switchable reactivity of acylated alpha, beta-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid.

Elena Angelini1, Cesarino Balsamini, Francesca Bartoccini, Simone Lucarini, Giovanni Piersanti.   

Abstract

Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18558761     DOI： 10.1021/jo800881u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

Authors:  Lindsay M Repka; Jane Ni; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

Review 2.  Dehydroamino acids: chemical multi-tools for late-stage diversification.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

3.  Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors:  Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2012-03-05       Impact factor: 15.419

4.  Overturning indolyne regioselectivities and synthesis of indolactam V.

Authors:  Sarah M Bronner; Adam E Goetz; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-02-25       Impact factor: 15.419

5.  Photocatalytic Reductive Olefin Hydrodifluoroalkylation Enabled by Tertiary Amine Reductants Compatible with Complex Systems.

Authors:  Jonathan D Ellefsen; Scott J Miller
Journal:  J Org Chem       Date:  2022-07-13       Impact factor: 4.198

6.  Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2.

Authors:  Noah F Fine Nathel; Tejas K Shah; Sarah M Bronner; Neil K Garg
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

7.  C-H methylation of heteroarenes inspired by radical SAM methyl transferase.

Authors:  Jinghan Gui; Qianghui Zhou; Chung-Mao Pan; Yuki Yabe; Aaron C Burns; Michael R Collins; Martha A Ornelas; Yoshihiro Ishihara; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-03-21       Impact factor: 15.419

Review 8.  Synthesis and bioactivity of secondary metabolites from marine sponges containing dibrominated indolic systems.

Authors:  Adriano Mollica; Marcello Locatelli; Azzurra Stefanucci; Francesco Pinnen
Journal:  Molecules       Date:  2012-05-21       Impact factor: 4.411

9.  Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Authors:  Michele Mari; Simone Lucarini; Francesca Bartoccini; Giovanni Piersanti; Gilberto Spadoni
Journal:  Beilstein J Org Chem       Date:  2014-08-26       Impact factor: 2.883

10.  Synthesis of constrained analogues of tryptophan.

Authors:  Elisabetta Rossi; Valentina Pirovano; Marco Negrato; Giorgio Abbiati; Monica Dell'Acqua
Journal:  Beilstein J Org Chem       Date:  2015-10-27       Impact factor: 2.883
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.