Literature DB >> 17630734

C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.

Barbora Bajtos1, Ming Yu, Hongda Zhao, Brian L Pagenkopf.   

Abstract

The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.

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Year:  2007        PMID: 17630734     DOI: 10.1021/ja067821+

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


  9 in total

1.  Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Authors:  John R Goodell; Jennifer L Poole; Aaron B Beeler; Jeffrey Aubé; John A Porco
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2.  Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers.

Authors:  Xiangbing Qi; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Polarity inversion of donor-acceptor cyclopropanes: disubstituted δ-lactones via enantioselective iridium catalysis.

Authors:  Joseph Moran; Austin G Smith; Ryan M Carris; Jeffrey S Johnson; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-10-31       Impact factor: 15.419

4.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

5.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

6.  Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

Authors:  Johannes Preindl; Shyamal Chakrabarty; Jérôme Waser
Journal:  Chem Sci       Date:  2017-08-25       Impact factor: 9.825

7.  Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Authors:  Vincent Pirenne; Emma G L Robert; Jerome Waser
Journal:  Chem Sci       Date:  2021-05-05       Impact factor: 9.825

8.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825

9.  Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor-Acceptor Cyclopropanes.

Authors:  Alesandere Ortega; Uxue Uria; Tomás Tejero; Liher Prieto; Efraim Reyes; Pedro Merino; Jose L Vicario
Journal:  Org Lett       Date:  2021-03-09       Impact factor: 6.072

  9 in total

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