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 language | English |
|---|---|
| Pages (from-to) | 4185-4188 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 7 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - 2005 Sep 15 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Itagaki, N., Kimura, M., Sugahara, T., & Iwabuchi, Y. (2005). Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization. Organic letters, 7(19), 4185-4188. https://doi.org/10.1021/ol051569d