Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.
The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.
Bow
William F
WF
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
Basak
Ashok K
AK
Jolit
Anais
A
Vicic
David A
DA
Tius
Marcus A
MA
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007097:Imines; D007659:Ketones