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Stereoselective Protonation of Boron Enolates

Thomas Haubenreich, Siegfried Hünig, Hans‐Joachim Schulz

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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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What this paper is about

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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Available 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.

Key concepts: Protonation, Trifluoroacetic acid, Boron, Acetic acid, Chemistry, Medicinal chemistry, Stereoselectivity, Organic chemistry

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