Role of reversible dimerization in reactions of amphoteric aziridine aldehydes.
Unprotected aziridine aldehydes belong to the amphoteric class of molecules by virtue of their dual nucleophilicity/electrophilicity. The dimeric nature of these molecules, brought together by a weak and reversible aminal "connection", was found to be an important element of reactivity control. We present evidence that reversible dimer dissociation is instrumental in aziridine aldehyde transformations. We anticipate further developments that will unveil other synthetic consequences of remote control of selectivity through forging reversible covalent interactions.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Naila
N
Assem
Ryan
R
Hili
Zhi
Z
He
Takahito
T
Kasahara
Brittany L
BL
Inman
Shannon
S
Decker
Andrei K
AK
Yudin
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D001388:Aziridines