Asymmetric Cu-catalyzed 1,6-conjugate addition of dialkylzinc reagents to 5-(3-aryl-2-propenylidene) Meldrum's acids

Tetrahedron Asymmetry

Volumn 17, Issue 21, 2006, Pages 2957-2959

  Fillion, Eric ^a   Wilsily, Ashraf ^a   Liao, E Ting ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; PROPYLENE; ZINC DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CONJUGATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 33845211504     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.11.009     Document Type: Article

References (28)

1. Asymmetric 1,4-conjugate addition reviews:. Feringa B.L., Naasz R., Imbos R., and Arnold L.A. In: Krause N. (Ed). Modern Organocopper Chemistry (2002), Wiley-VCH, Weinheim, Germany 224-258
2. Alexakis A., and Benhaim C. Eur. J. Org. Chem. 67 (2002) 3221-3236
3. Krause N., and Hoffmann-Röder A. Synthesis (2001) 171-196
4. Sibi M.P., and Manyem S. Tetrahedron 56 (2000) 8033-8061
5. For reviews on catalytic asymmetric synthesis of all-carbon quaternary carbon centers:. Trost B.M., and Jiang C. Synthesis (2006) 369-396
6. Douglas C.J., and Overman L.E. Proc. Natl. Acad. Sci. USA 101 (2004) 5363-5367
7. Asymmetric 1,4-conjugate addition forming all-carbon quaternary centres:. Martin D., Kehrli S., d'Augustin M., Clavier H., Mauduit M., and Alexakis A. J. Am. Chem. Soc. 128 (2006) 8416-8417
8. Lee K., Brown K.M., Hird A.W., and Hoveyda A.H. J. Am. Chem. Soc. 128 (2006) 7182-7184
9. d'Augustin M., Palais L., and Alexakis A. Angew. Chem., Int. Ed. 44 (2005) 1376-1378
10. Hird A.W., and Hoveyda A.H. J. Am. Chem. Soc. 127 (2005) 14988-14989
11. Wu J., Mampreian D.M., and Hoveyda A.H. J. Am. Chem. Soc. 127 (2005) 4584-4585
12. Mauleón P., and Carretero J.C. Chem. Commun. (2005) 4961-4963
13. Fuchs N., d'Augustin M., Humam M., Alexakis A., Taras R., and Gladiali S. Tetrahedron: Asymmetry 16 (2005) 3143-3146
14. For reviews on 1,6-conjugate addition:. Krause N., and Thorand S. Inorg. Chim. Acta 296 (1999) 1-11
15. Krause N., and Gerold A. Angew. Chem., Int. Ed. 36 (1997) 186-204
16. Fredrick M.A., and Hulce M. Tetrahedron 53 (1997) 10197-10227
17. Marshall J.A., Ruden R.A., Hirsch L.K., and Phillippe M. Tetrahedron Lett. 41 (1971) 3795-3998
18. Nishimura T., Yasuhara Y., and Hayashi T. Angew. Chem., Int. Ed. 45 (2006) 1-4
19. Fukuhara K., and Urabe H. Tetrahedron Lett. 46 (2005) 603-606
20. de la Herrán G., Murcia C., and Csákÿ A.G. Org. Lett. 7 (2005) 5629-5632
21. Hayashi T., Tokunaga N., and Inoue K. Org. Lett. 6 (2004) 305-307
22. Hayashi T., Yamamoto S., and Tokunaga N. Angew. Chem., Int. Ed. 44 (2005) 4224-4227
23. Fillion E., and Wilsily A. J. Am. Chem. Soc. 128 (2006) 2774-2775
24. Feringa B.L. Acc. Chem. Res. 33 (2000) 346-353
25. Feringa B.L., Pineschi M., Arnold L.A., Imbos R., and de Vries A.H.M. Angew. Chem., Int. Ed. 36 (1997) 2620-2623
26. Asymmetric synthesis of tertiary carbon centers from alkylidene Meldrum's acids and dialkylzinc reagents:. Knöpfel T.F., Zarotti P., Ichikawa T., and Carreira E.M. J. Am. Chem. Soc. 127 (2005) 9682-9683
27. Watanabe T., Knöpfel T.F., and Carreira E.M. Org. Lett. 5 (2003) 4557-4558
28. 4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel using a combination of EtOAc and hexanes or petroleum ether (35-60 °C) as eluent to yield the desired product. HPLC equipped with a chiral column (OD-H or AD-H) was used to measure the enantiomeric excess of the products. The racemates were prepared using the corresponding Grignard reagent (2.5 equiv) in THF at -40 °C.