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Enantioselective deprotonation of symmetrical epoxides was studied by using chiral lithium amide, prepared from (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine and butyllithium. Chiral allylic alcohols were obtained with moderate to high enantiomeric excesses (ee’s) (41–92% ee) from several cyclic and acyclic epoxides employing lithium (S)-2-(1-pyrrolidinylmethyl)pyrrolidide in tetrahydrofuran (THF) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

Asymmetric Trasformation of Symmetrical Epoxides to Allylic Alcohols by Lithium (S)-2-(N,N-Disubstituted aminomethyl)pyrrolidide