Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines viaL-phenylalanine-derived dihydroisoquinoline N-oxides

Jesús Flores-Ferrándiz; Nicholas Carter; Maria José González-Soria; Malgorzata Wasinska; Daniel Gill; Beatriz Maciá; Vittorio Caprio

doi:10.1039/C8OB02007H

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides†

Jesús Flores-Ferrándiz,^a Nicholas Carter,^a Maria José González-Soria,^a Malgorzata Wasinska,^a Daniel Gill,^a Beatriz Maciá

*^a and Vittorio Caprio*^a

Author affiliations

* Corresponding authors

^a School of Science and the Environment, Manchester Metropolitan University, All Saints Campus, Oxford Road, Manchester, UK
E-mail: b.macia-ruiz@mmu.ac.uk, v.caprio@mmu.ac.uk

Abstract

The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

This article is part of the themed collection: Synthetic methodology in OBC

Download options Please wait...

Supplementary files

Supplementary information PDF (3667K)

Article information

DOI: https://doi.org/10.1039/C8OB02007H
Article type: Paper
Submitted: 16 Aug 2018
Accepted: 10 Sep 2018
First published: 12 Sep 2018
This article is Open Access

Download Citation

Org. Biomol. Chem., 2018,16, 6961-6968

Permissions

Request permissions

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines viaL-phenylalanine-derived dihydroisoquinoline N-oxides

J. Flores-Ferrándiz, N. Carter, M. J. González-Soria, M. Wasinska, D. Gill, B. Maciá and V. Caprio, Org. Biomol. Chem., 2018, 16, 6961 DOI: 10.1039/C8OB02007H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines viaL-phenylalanine-derived dihydroisoquinoline N-oxides

Social activity

Search articles by author

Spotlight

Advertisements