Asymmetric catalytic C-H activation applied to the synthesis of syn-aldol products

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4153-4155

  Davies, Huw M L ^a   Antoulinakis, Evan G ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001250094     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006671j     Document Type: Article

References (27)

1. Doyle, M. P.; McKervey, M. A.; Ye, T. In Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998; pp 112-162.
2. Davies, H. M. L.; Panaro, S. A. Tetrahedron 2000, 56, 4871.
3. (a) Davies, H. M. L.; Church, L. A.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1989, 30, 4653.
4. (b) Davies, H. M. L.; Rusiniak, L. Tetrahedron Lett. 1998, 39, 8811.
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11. For general reviews, see: (a) Davies, H. M. L. Aldrichimica Acta 1997, 30, 105.
12. (b) Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459.
13. (a) Davies, H. M. L.; Hansen, T. J. Am. Chem. Soc. 1997, 119, 9075.
14. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233.
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17. (e) Axten, J. M.; Ivy, R.; Krim, L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
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19. (g) Muller, P.; Tohill, S. Tetrahedron 2000, 56, 1725.
20. (h) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
21. For a general review, see: Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem., in press.
22. For reviews of catalytic enantioselective aldol reactions, see: (a) Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357.
23. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin: 1999; Vol. III, pp 997-1066.
24. 1H NMR of the crude reaction mixtures and the products were not sufficiently stable for analysis by GCMS. Enantiomeric excess (ee) was determined by HPLC using a Chiralcel OD column and 2-propanol (0.8% or 1.0%) in hexane as the eluent.
25. Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. G. Tetrahedron Lett. 1998, 39, 4417.
26. Ahn, M.; Tanaka, K.; Fuji, K. J. Chem. Soc., Perkin Trans. 1 1998, 2, 185.
27. a, indicating a syn relative stereochemistry for all the insertion products.