Synthesis of Optically Active 5-Substituted-2-pyrrolidinone Derivatives Having Atropisomeric Structure and 3,5-Cis-Selective Reaction of Their Enolates with Electrophiles
- 1 February 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (4) , 1108-1114
- https://doi.org/10.1021/jo991578y
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-pyrrolidinone 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.Keywords
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