Asymmetric route to pyridines bearing a highly functionalized 2-alkyl substituent by aziridine ring-opening reactions.
The aziridine prepared from the 2-pyridineimine derived from (S)-valinol underwent ring-opening by attack of nitrogen, sulfur, and oxygen nucleophiles. Complete or prevalent regioselectivity was obtained using cerium trichloride heptahydrate as a catalyst. In some cases, the N-substituent could be removed by an oxidative protocol.
Savoia
Diego
D
Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, 40126 Bologna, Italy. diego.savoia@unibo.it
Alvaro
Giuseppe
G
Di Fabio
Romano
R
Gualandi
Andrea
A
D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D005021:Ethylamines; D011725:Pyridines; C033132:aziridine