☆ 4.4 Article

Facile synthesis of α-methylidene-γ-butyrolactones: intramolecular Rauhut-Currier reaction promoted by chiral acid base organocatalysts

TETRAHEDRON (2013)

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Journal

TETRAHEDRON
Volume 69, Issue 3, Pages 1202-1209

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.11.046

Keywords

Rauhut-Currier; Enantioselective; Organocatalysts; alpha-Methylidene-gamma-butyrolactones; Intramolecular

Categories

Chemistry, Organic

Funding

  1. CREST project of the Japan Science and Technology Corporation (JST)
  2. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
  3. Deutsche Forschungsgemeinschaft
  4. Grants-in-Aid for Scientific Research [22350041, 24590009, 10F00346, 24106726, 24105518] Funding Source: KAKEN

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The acid-base organocatalyzed intramolecular Rauhut-Currier (RC) reaction of the dienone enolates has been developed. The enantioselective RC process produces the highly functionalized alpha-methylidene-gamma-butyrolactones as a single diastereomer with up to 98% ee. (C) 2012 Elsevier Ltd. All rights reserved.

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