EventsMOL2NET'16, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 2nd ed.
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Published
with-doi10.3390/MOL2NET-02-H003
This submission belongs to the session 02. CHEMBIOMOL-02: Chem. Biol. & Med. Chem. Workshop, Rostock, Germany-Bilbao, Spain-Galveston, Texas, USA, 2016 of the event MOL2NET'16, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 2nd ed.
Published date
05 Feb, 2016
Citation
Esther Lete, Nuria Sotomayor, Eider Aranzamendi Uruburu, Brønsted acid catalyzed enantioselective inter and intramolecular α-amidoalkylation reactions in the synthesis of isoquinoline derivatives, in Proceedings of MOL2NET'16, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 2nd ed., 15 October–20 October 2022, MDPI: Basel, Switzerland, doi: 10.3390/MOL2NET-02-H003
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Brønsted acid catalyzed enantioselective inter and intramolecular α-amidoalkylation reactions in the synthesis of isoquinoline derivatives

Eider Aranzamendi Uruburu 1
Nuria Sotomayor 1
Esther Lete 1
1. Department of Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Bilbao, Spain.
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
Manuscript
OC3. Eider Aranzamendi.pdf
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