4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 42, Pages 5435-5437

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.07.128

Keywords

Hantzsch cyclization; Thiazole; Thiopeptides; Proline

Funding

  1. Ministerio de Ciencia e Innovacion, CICYT [CTQ2009-07758]
  2. Generalitat de Catalunya [2009SGR 1024]
  3. ISCIII
  4. Ministerio de Ciencia e Innovacion

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(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. (C) 2011 Elsevier Ltd. All rights reserved.

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