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

Masatoshi Asami | Zendy

Open Access

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

Author(s) -

Masatoshi Asami

Publication year - 1990

Publication title -

bulletin of the chemical society of japan

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.145

H-Index - 99

eISSN - 1348-0634

pISSN - 0009-2673

DOI - 10.1246/bcsj.63.721

Subject(s) - chemistry , allylic rearrangement , lithium (medication) , medicinal chemistry , epoxide , organic chemistry , stereochemistry , catalysis , medicine , endocrinology

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).

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