4.5 Article

Diastereodivergent Synthesis of Chiral vic-Disubstituted-Cyclobutane Scaffolds: 1,3-Amino Alcohol and 1,3-Diamine Derivatives - Preliminary Use in Organocatalysis

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 8, Pages 1425-1433

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201307

Keywords

Synthetic methods; Organocatalysis; Asymmetric catalysis; Michael addition; Regioselectivity; Amino alcohols; Amines

Funding

  1. Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2010-15408/BQU]
  2. Generalitat de Catalunya [2009SGR-733]

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The synthesis of chiral cyclobutane containing 1,3-amino alcohols and 1,3-diamines has been accomplished in an efficient and diastereodivergent manner from a common chiral precursor. Regioselective manipulation of functional groups in the prepared products provides an easy entry to several derivatives, such as thioureas. Preliminary results on the use of these compounds as bifunctional organocatalysts are reported.

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