Premium
Chiral Organometallic Reagents, XX. An Enantiomerically Enriched (α‐Phenylselenoalkyl)magnesium Compound
Author(s) -
Klute Wolfgang,
Krüger Michael,
Hoffmann Reinhard W.
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290607
Subject(s) - chemistry , magnesium , reagent , enantiomer , kinetic resolution , chelation , group 2 organometallic chemistry , lithium (medication) , grignard reagent , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , molecule , catalysis , medicine , endocrinology
α‐Selenoalkyl Grignard reagents 2 are chiral. On reaction with the magnesium chelate 3a of α‐benzyloxypropionaldehyde they show significant degrees of kinetic resolution, especially when the reactions are run in CH 2 Cl 2 . Under these conditions, racemic 2 was resolved by reaction with 0.59 equivalents of 3a at temperatures below –20°C. The remaining 2 had an enantiomer enrichment of 80–86% e.e. (as found by trapping). Hence, 2 has a considerably higher configurational stability than its lithium counterpart 1 .