Chiral Organometallic Reagents, XX. An Enantiomerically Enriched (α‐Phenylselenoalkyl)magnesium Compound | Zendy

Klute Wolfgang | Zendy; Krüger Michael | Zendy; Hoffmann Reinhard W. | Zendy

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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 .

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