Synthesis of optically active 5-substituted-2-pyrrolidinone derivatives having atropisomeric structure and 3,5-cis-selective reaction of their enolates with electrophiles
Optically pure forms (>/=98% ee) of N-(o-tert-butylphenyl)-5-(methoxymethyl)-2-pyrrolidinone having atropisomerism and N-(o-tert-butyldiphenylsiloxyphenyl)-5-(methoxymethyl)-2-pyrrolidinon e having an atropisomerism-like structure were prepared from ortho-substituted aniline derivatives and (S)-5-(methoxymethyl)butyrolactone in a stereoselective manner. The reactions of Li-enolates from these lactams with various electrophiles and subsequent dearylation of the products gave 3, 5-cis-disubstituted-2-pyrrolidinone derivatives.
Fujita
M
Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan.
Kitagawa
O
Yamada
Y
Izawa
H
Hasegawa
H
Taguchi
T