Asymmetric α-2-tosylethenylation of N,N-dialkyl-L-amino acid esters via the formation of non-racemic ammonium enolates

Asymmetric α-2-tosylethenylation of N,N-dialkyl-L-amino acid esters via the formation of non-racemic ammonium enolates

Asymmetric α-2-tosylethenylation of (S)-2-(pyrrolidin-1-yl)propanoic acid esters was shown to produce good yields with high enantioselectivities. The reaction proceeds via the formation of a non-racemic ammonium enolate without an external source of chirality.

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Veröffentlicht in:Organic & biomolecular chemistry 2012-01, Vol.10 (2), p.339-345
Hauptverfasser: Tayama, Eiji, Igarashi, Tomohito, Iwamoto, Hajime, Hasegawa, Eietsu
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemistry
Esters - chemistry
Molecular Structure
Quaternary Ammonium Compounds - chemical synthesis
Quaternary Ammonium Compounds - chemistry
Stereoisomerism
Sulfones - chemistry
Toluene - analogs & derivatives
Toluene - chemistry
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Zusammenfassung:Asymmetric α-2-tosylethenylation of (S)-2-(pyrrolidin-1-yl)propanoic acid esters was shown to produce good yields with high enantioselectivities. The reaction proceeds via the formation of a non-racemic ammonium enolate without an external source of chirality.
ISSN:1477-0539
DOI:10.1039/c1ob06074k