Collect. Czech. Chem. Commun. 2011, 76, 815-828
https://doi.org/10.1135/cccc2011013
Published online 2011-06-17 11:33:18

An approach to preparation of trans-DHQs via ring-opening of meso-N-sulfonylaziridines

Jens Nolsøea, David Riegertb, Paul Müllerb,* and David Tannera,*

a Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark
b Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland

Abstract

As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral non-racemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

Keywords: Desymmetrization; Carbon nucleophiles; meso-Aziridines; Yb-catalysis; trans-DHQs; Alkaloids; Metathesis; Synthetic methods.

References: 24 live references.

This article is part of virtual issue Prof. Pavel Kočovský, FRSE
60th Birthday.