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Chiral Epoxides by Desymmetrizing Deprotonation of meso ‐Epoxides
Author(s) -
Hodgson David M.,
Gras Emmanuel
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020703)41:13<2376::aid-anie2376>3.0.co;2-q
Subject(s) - electrophile , deprotonation , enantioselective synthesis , ligand (biochemistry) , lithium (medication) , chemistry , sparteine , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , ion , medicine , biochemistry , receptor , endocrinology
Simple meso ‐epoxides can be asymmetrically functionalized : Ligand‐assisted direct hydrogen–lithium exchange allows the generation of destabilized oxiranyl lithium species and their subsequent trapping by a wide array of electrophiles (see scheme; E=group formed by addition of electrophile). When carried out in the presence of (−)‐sparteine as ligand, this reaction provides a new enantioselective route to epoxides.