ENANTIOFACE-DIFFERENTIATING ADDITION OF A CHIRAL ARYLLITHIUM REAGENT TO ALDEHYDES
- 5 January 1980
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 9 (1), 17-20
- https://doi.org/10.1246/cl.1980.17
Abstract
A chiral aryllithium reagent was prepared by treating a chiral aminal, derived from (S)-2-(anilinomethyl)pyrrolidine and o-bromobenzaldehyde, with n-butyl lithium. The chiral reagent reacted highly enantioface selectively with aliphatic aldehydes and, on hydrolysis of the resulting aminals, various 3-alkyl-1-hydroxy-2-oxaindanes with high enantiomeric excesses were obtained. The oxidation of 3-butyl-1-hydroxy-2-oxaindane with silver oxide afforded (S)-3-butylphthalide, an essential oil of celery, with 88% e.e..Keywords
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- Synthesis of δ‐Lactones from GlutaraldehydeHelvetica Chimica Acta, 1972