Br&oslash;nsted acid catalyzed enantioselective inter and intramolecular &alpha;-amidoalkylation reactions in the synthesis of isoquinoline derivatives

Eider Aranzamendi Uruburu; Nuria Sotomayor; Esther Lete

doi:10.3390/MOL2NET-02-H003

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Enantioselective Synthesis of Chiral Proline Derivatives

Brønsted acid catalyzed enantioselective inter and intramolecular α-amidoalkylation reactions in the synthesis of isoquinoline derivatives

Eider Aranzamendi Uruburu

^*,

Nuria Sotomayor

Esther Lete

¹ Department of Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Bilbao, Spain.

Published: 05 February 2016 by MDPI in MOL2NET'16, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 2nd ed. congress CHEMBIOMOL-02: Chem. Biol. & Med. Chem. Workshop, Rostock, Germany-Bilbao, Spain-Galveston, Texas, USA, 2016

https://doi.org/10.3390/MOL2NET-02-H003

Abstract:

The a-amidoalkylation reaction of aromatic systems using N-acyliminium ions as electrophiles is one of the most attractive methods for C-C bond formation in heterocyclic chemistry and has found widespread application in natural products synthesis.[1] A significant progress in the application of enantioselective versions of a-amidoalkylation reactions has been marked by the development of chiral Brønsted acids (mainly BINOL derived phosphoric acids) and hydrogen bond donors (mainly ureas and thioureas).In this context, we have shown that BINOL-derived chiral Brønsted acids catalyze the intermolecular a-amidoalkylation of a bicyclic a-hydroxylactams, obtained by Parham cyclyzation of the corresponding N-phnethylimides, with indole derivatives. Thus, a convenient enantioselective synthesis of 12b-substituted isoindoloisoquinolines (ee up to 95 %) has been achieved.[2]

[1] Martínez-Estibalez, U.; Gómez-SanJuan, A.; García-Calvo, O.; Lete, E.; Sotomayor, N. Eur. J. Org. Chem. 2011, 3610

[2] Aranzamendi, E.; Sotomayor, N; Lete,. E. J. Org. Chem. 2012, 77, 2986.

Keywords: alfa-amidoalkylation; C-C bond formation; Heterocyclic chemistry; Chiral Brønsted acids; Enantioselective synthesis

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Eider Aranzamendi Uruburu

Nuria Sotomayor

Esther Lete