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 |
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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