Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis

Author:

Trubitsõn Dmitri1,Martõnova Jevgenija1,Erkman Kristin1,Metsala Andrus1,Saame Jaan2,Kõster Kristjan2,Järving Ivar1,Leito Ivo2,Kanger Tõnis1ORCID

Affiliation:

1. Department of Chemistry and Biotechnology, Tallinn University of Technology

2. Institute of Chemistry, University of Tartu

Abstract

An asymmetric phase-transfer-catalyzed N-alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.

Funder

Haridus- ja Teadusministeerium

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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