Aza-Henry Reactions on C-Alkyl Substituted Aldimines.
The reactivity of C-CH₃ substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF₃ aldimines, they gave the aza-Henry addition only when ZrCl₄ was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity.
Dipartimento di Chimica, Universit&#224; degli Studi di Roma "La Sapienza", P.le Aldo Moro 5, I-00185 Roma, Italy. alessia.pelagalli@uniroma1.it.
Alessia
A
Pelagalli
Dipartimento di Chimica, Universit&#224; degli Studi di Roma "La Sapienza", P.le Aldo Moro 5, I-00185 Roma, Italy. lucio.pellacani@uniroma1.it.
Lucio
L
Pellacani
Dipartimento di Chimica, Universit&#224; degli Studi di Roma "La Sapienza", P.le Aldo Moro 5, I-00185 Roma, Italy. eliasca93@gmail.com.
Elia
E
Scandozza
Dipartimento di Chimica, Universit&#224; degli Studi di Roma "La Sapienza", P.le Aldo Moro 5, I-00185 Roma, Italy. stefania.fioravanti@uniroma1.it.
Stefania
S
Fioravanti
D000473:Alkanes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D000473:Alkanes; D000588:Amines; D002712:Chlorides; D002244:Carbon; D015040:Zirconium; C429984:zirconium chloride
amines; carbon–carbon bond formation; nitro compounds