Asymmetric trasformation of symmetrical epoxides to allylic alcohols by lithium (S)-2-(N,N-disubstituted aminomethyl)pyrrolidide.
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概要
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Enantioselective deprotonation of symmetrical epoxides was studied by using chiral lithium amide, prepared from (<I>S</I>)-2-(<I>N</I>,<I>N</I>-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 (<I>S</I>)-2-(1-pyrrolidinylmethyl)pyrrolidide in tetrahydrofuran (THF) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
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