Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

Noriaki Itagaki, Mari Kimura, Tsutomu Sugahara, Yoshiharu Iwabuchi

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

(Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1] nonan-2-one.

Original languageEnglish
Pages (from-to)4185-4188
Number of pages4
JournalOrganic letters
Volume7
Issue number19
DOIs
Publication statusPublished - 2005 Sep 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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