193475-95-5Relevant academic research and scientific papers
Highly chemoselective formation of aldehyde enamines under very mild reaction conditions
Belanger, Guillaume,Dore, Michael,Menard, Frederic,Darsigny, Veronique
, p. 7481 - 7484 (2007/10/03)
Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfull
An Unusual Acyliminium Cyclization and Other Drawbacks during an Attempted Synthesis of a Chiral Primary α-Phosphinoalkanamine
Christoffers, Jens
, p. 845 - 852 (2007/10/03)
Studies towards the synthesis of a chiral primary α-phosphinoalkanamine 1a are reported. O-Activated, N-carbamate-protected phenylalaninol 3a did not undergo 5N reaction with KPPh2: instead, after TV-deprotonalion, intramolecular substitution led to formation of the aziridine derivative 5a (Scheme 2). N-Phthalimido-protected. O-activated phenylalaninol 3b also underwent an intramolecular process on treatment with KPPh2, i.e., an unusual aryl-acyliminium cyclization furnishing the (epoxymethano)isoindolo[1,2-a]isoquinolinone 7 (Scheme 3). In a reaction with KPPh2, the N,N-dibenzyl-protected and activated phenylalaninol 3d finally yielded the intermolecular SN reaction product 2a (Scheme 4). However, debenzylation by catalytic hydrogenation turned out to be impossible.
