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.
|Journal||Collection of Czechoslovak Chemical Communications|
|Publication status||Published - 2011|
Bibliographical noteDedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.
- Synthetic methods
Nolsøe, J. M. J., Riegert, D., Müller, P., & Tanner, D. A. (2011). An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs. Collection of Czechoslovak Chemical Communications, 76(7), 815-828. https://doi.org/10.1135/cccc2011013