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

Publication: Research - peer-reviewJournal article – Annual report year: 2011

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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.
Original languageEnglish
JournalCollection of Czechoslovak Chemical Communications
Publication date2011
Volume76
Journal number7
Pages815-828
ISSN0010-0765
DOIs
StatePublished

Bibliographical note

Dedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.

CitationsWeb of Science® Times Cited: 0

Keywords

  • Synthetic methods, Alkaloids, Desymmetrization, Metathesis, trans-DHQs, Yb-catalysis, meso-Aziridines
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