Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine

( S)-2-(4-Bromo-2,4′-bithiazole)-1-( tert-butoxycarbonyl)pyrrolidine ( ( S )- 1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone 3 and thioamide ( S )- 4 were used. Further conversion of ( S )- 1 into trimeth...

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Veröffentlicht in:	Tetrahedron letters 2011-10, Vol.52 (42), p.5435-5437
Hauptverfasser:	Just-Baringo, Xavier, Bruno, Paolo, Albericio, Fernando, Álvarez, Mercedes
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics Antibiòtics Chemical reactions Chemistry Compostos heterocíclics Conversion Derivatives Enantiomers Enantiòmers Exact sciences and technology Hantzsch cyclization Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Natural products Organic chemistry Peptide synthesis Preparations and properties Productes naturals Proline Synthesis (chemistry) Síntesi de pèptids Tetrahedrons Thiazole Thiopeptides
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Beschreibung
Zusammenfassung:	( S)-2-(4-Bromo-2,4′-bithiazole)-1-( tert-butoxycarbonyl)pyrrolidine ( ( S )- 1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone 3 and thioamide ( S )- 4 were used. Further conversion of ( S )- 1 into trimethyltin derivative ( S )- 2 broadens the scope for further cross-coupling reactions.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.07.128