Journal
TETRAHEDRON-ASYMMETRY
Volume 23, Issue 11-12, Pages 859-866Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2012.05.026
Keywords
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Research Foundation for Pharmaceutical Sciences
- Grants-in-Aid for Scientific Research [23390003] Funding Source: KAKEN
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A novel catalytic asymmetric synthetic method for making spirocyclohexadienones with an all-carbon quaternary spirocenter was developed based on the Pd-catalyzed intramolecular ipso-Friedel-Crafts allylic alkylation of phenols. When 5 mol % of the Pd catalyst and 12 mol % of (-)-9-NapBN (-)-3e were used, the spirocyclic adduct was obtained with up to 93% ee, albeit with low chemical yield. On the other hand, when using 6 mol% of the Trost ligand (R,R)-3k, the spirocyclic adducts were obtained in good yields with up to 89% ee (diastereoselectivity = 9.2:1). (c) 2012 Elsevier Ltd. All rights reserved.
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