Synthesis of optically active 5-substituted-2-pyrrolidinone derivatives having atropisomeric structure and 3,5-cis-selective reaction of their enolates with electrophiles |
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Authors: | Fujita Kitagawa Yamada Izawa Hasegawa Taguchi |
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Institution: | Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan. |
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Abstract: | 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. |
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