How does electrostatic activation control iminium-catalyzed cyclopropanations?
Prediction of lg k = s(N+E) verified: In contrast to previous statements, ordinary alpha,beta-unsaturated iminium ions do react with sulfur ylides. Electrostatic interactions accelerate the reactions by a factor of more than 10(5) and are responsible for the high stereoselectivity.
Lakhdar
Sami
S
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377 München, Germany.
Appel
Roland
R
Mayr
Herbert
H
D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D055672:Static Electricity; D013237:Stereoisomerism
D007097:Imines