Asymmetric α-2-tosylvinylation of in situ-generated N-2-tosylvinyl proline-derived ammonium ylides

Asymmetric α-2-tosylvinylation of N-substituted proline esters using ethynyl tolyl sulfone as an electrophile was shown to proceed in good yield with high enantioselectivities without the addition of any bases. The reaction proceeds via the formation of N-2-tosylvinyl ammonium ylides.

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Bibliographische Detailangaben
Veröffentlicht in:	Tetrahedron letters 2011-04, Vol.52 (15), p.1819-1821
Hauptverfasser:	Igarashi, Tomohito, Tayama, Eiji, Iwamoto, Hajime, Hasegawa, Eietsu
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino acid Asymmetric synthesis Asymmetry Chemistry Esters Exact sciences and technology Formations Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Proline Sulfones Tetrahedrons Ylide Zwitterion
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Beschreibung
Zusammenfassung:	Asymmetric α-2-tosylvinylation of N-substituted proline esters using ethynyl tolyl sulfone as an electrophile was shown to proceed in good yield with high enantioselectivities without the addition of any bases. The reaction proceeds via the formation of N-2-tosylvinyl ammonium ylides.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.02.040