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One-carbon bridge stereocontrol in robinson annulations leading to bicyclo[3.3.1]nonanes.
- Source :
-
Organic letters [Org Lett] 2010 Mar 19; Vol. 12 (6), pp. 1232-5. - Publication Year :
- 2010
-
Abstract
- The one-carbon bridge stereochemistry of bicyclo[3.3.1]nonane products formed in the Robinson annulation reactions of 2-substituted cyclohex-2-enones was investigated. In contrast to previous reports, it was found that the major diastereomer formed places the one-carbon bridge substituent anti to the beta-keto ester/amide unit introduced in the Robinson annulation. This stereoselectivity appears to be kinetically controlled. In the case of a beta-keto amide product derived from carvone, it was demonstrated, through base-catalyzed epimerization, that thermodynamic control favors the syn isomer.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 12
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 20180523
- Full Text :
- https://doi.org/10.1021/ol1000878