Ring Opening/C–N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines

2011 ◽  
Vol 13 (16) ◽  
pp. 4256-4259 ◽  
Author(s):  
Manas K. Ghorai ◽  
Y. Nanaji ◽  
A. K. Yadav
Keyword(s):  
Ring Opening ◽  
Enantioselective Synthesis ◽  
Carbon Nucleophiles

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

2011 ◽  
Vol 76 (7) ◽  
pp. 815-828 ◽  
Author(s):  
Jens Nolsøe ◽  
David Riegert ◽  
Paul Müller ◽  
David Tanner
Keyword(s):  
Ring Opening ◽  
Enantioselective Synthesis ◽  
Carbon Nucleophiles

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.

Regioselective ring opening of thiomalic acid anhydrides by carbon nucleophiles. Synthesis and X-ray structure elucidation of novel thiophenone derivatives

Tetrahedron ◽  
2009 ◽  
Vol 65 (18) ◽  
pp. 3711-3716 ◽  
Author(s):  
Stefanos Kikionis ◽  
Vickie McKee ◽  
John Markopoulos ◽  
Olga Igglessi-Markopoulou
Keyword(s):  
Ring Opening ◽  
Structure Elucidation ◽  
X Ray ◽  
Carbon Nucleophiles ◽  
Acid Anhydrides
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