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New Insights into the Classic Chiral Grignard Reagent (1 R ,2 S ,5 R )‐Menthylmagnesium Chloride
Author(s) -
Beckmann Jens,
Dakternieks Dainis,
Dräger Martin,
Duthie Andrew
Publication year - 2006
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/anie.200602091
Subject(s) - reagent , electrophile , diastereomer , grignard reagent , chemistry , nucleophile , grignard reaction , chloride , medicinal chemistry , organic chemistry , catalysis
Two in one : An equimolar mixture of the diastereomers (1 R ,2 S ,5 R )‐MenMgCl and (1 S ,2 S ,5 R )‐NeomMgCl is formed from reaction of Mg with either menthyl (Men) or neomenthyl (Neom) chloride. Once formed, each component of the Grignard reagent is configurationally stable. Reaction with electrophiles generally yields products from attack by the more nucleophilic menthyl portion of the Grignard reagent.