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Journal article

An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs

From

Department of Chemistry, Technical University of Denmark1

University of Geneva2

Organic Chemistry, Department of Chemistry, Technical University of Denmark3

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 nonracemic ligands, nitrile 13 was obtained with an ee up to 40%.

Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

Language: English
Year: 2011
Pages: 815-828
ISSN: 12126950 and 00100765
Types: Journal article
DOI: 10.1135/cccc2011013
ORCIDs: Tanner, David Ackland

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