Stereoselective Protonation of Boron Enolates
Thomas Haubenreich, Siegfried Hünig, Hans‐Joachim Schulz
Abstract
Thomas Haubenreich, Siegfried Hünig, Hans‐Joachim Schulz
Abstract
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.
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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.
Key concepts: Protonation, Trifluoroacetic acid, Boron, Acetic acid, Chemistry, Medicinal chemistry, Stereoselectivity, Organic chemistry