Stereoselective Protonation of Boron Enolates

Stereoselective Protonation of Boron Enolates

Due to the different coordinations of acetic acid and trifluoroacetic acid to the boron atom of the enolate 1, two reaction mechanisms result for the protonation of 1. The protonation with acetic acid leads to an enrichment of the (R) isomer (R)‐2. while with trifluoroacetic acid (S)‐2 is favored. R...

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Veröffentlicht in:Angewandte Chemie (International ed.) 1993-03, Vol.32 (3), p.398-399
Hauptverfasser: Haubenreich, Thomas, Hünig, Siegfried, Schulz, Hans-Joachim
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Beschreibung
Zusammenfassung:Due to the different coordinations of acetic acid and trifluoroacetic acid to the boron atom of the enolate 1, two reaction mechanisms result for the protonation of 1. The protonation with acetic acid leads to an enrichment of the (R) isomer (R)‐2. while with trifluoroacetic acid (S)‐2 is favored. R* = isopinocampheyl.
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.199303981