Lithiation of N-alkyl-(o-tolyl)aziridine: stereoselective synthesis of isochromans.
The lithiation reaction of o-tolylaziridine 1 has been investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a-j. The hydroxyalkylated derivatives 2d-j were converted into important scaffolds such as isochromans 3a-d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine.
Dammacco
Mariangela
M
Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi C.I.N.M.P.I.S., Via E. Orabona 4, I-70125-Bari, Italy.
Degennaro
Leonardo
L
Florio
Saverio
S
Luisi
Renzo
R
Musio
Biagia
B
Altomare
Angela
A
D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D002839:Chromans; C033132:aziridine; D008094:Lithium