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

Flores-Ferrándiz, Jesús, Carter, Nicholas, González-Soria, Maria José, Wasinska, Malgorzata, Gill, Daniel, Maciá, Beatriz and Caprio, Vittorio (2018) Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides. Organic and Biomolecular Chemistry, 16 (38). pp. 6961-6968. ISSN 1477-0539

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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.

Item Type:	Article
Peer-reviewed:	Yes
Date Deposited:	03 Oct 2018 13:27
Publisher:	Royal Society of Chemistry
Additional Information:	This is an Open Access article published by and copyright The Royal Society of Chemistry 2018.
Divisions:	Faculties > Science and Engineering
Subject terms:	0304 Medicinal And Biomolecular Chemistry, 0305 Organic Chemistry, 1115 Pharmacology And Pharmaceutical Sciences, Organic Chemistry
URI:	https://e-space.mmu.ac.uk/id/eprint/621550
DOI:	https://doi.org/10.1039/c8ob02007h
ISSN	1477-0539

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