Organocatalytic Entry to Chiral Bicyclo[3.n.1]alkanones via Direct Asymmetric Intramolecular Aldolization

Organocatalytic Entry to Chiral Bicyclo[3.n.1]alkanones via Direct Asymmetric Intramolecular Aldolization

The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and endo-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 e...

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Veröffentlicht in:Organic letters 2005-09, Vol.7 (19), p.4185-4188
Hauptverfasser: Itagaki, Noriaki, Kimura, Mari, Sugahara, Tsutomu, Iwabuchi, Yoshiharu
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Cyclization
Molecular Structure
Stereoisomerism
Substrate Specificity
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Zusammenfassung:The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and endo-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051569d