Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of β-ketoesters and unsaturated N-acylthiazolidinethiones

Journal of the American Chemical Society

Volumn 127, Issue 31, 2005, Pages 10816-10817

  Evans, David A ^a   Thomson, Regan J ^a   Franco, Francisco ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA OXOCARBOXYLIC ACID ESTER; DIHYDROPYRONE DERIVATIVE; ESTER; FUMARIC ACID; LEWIS ACID; N ACYLTHIAZOLIDINETHIONE DERIVATIVE; NICKEL; PYRONE DERIVATIVE; THIAZOLIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; COMPLEX FORMATION; ENANTIOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY;

ESTERS; MODELS, MOLECULAR; NAPHTHALENES; NICKEL; STEREOISOMERISM; THIAZOLES;

EID: 23744458820     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053820q     Document Type: Article

References (26)

1. For reviews, see: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999: Vol. 3, Chapter 31.1.
2. (b) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171-196.
3. For recent examples, see: (c) Wang, E.; Wang, J.; Ji, H. Angew. Chem., Int. Ed. 2005, 44, 1369-1371.
4. (d) Suga, H.; Kitamura, T.; Kakchi, A.; Baba, T. J. Chem. Soc., Chem. Commun. 2004, 1414-1415.
5. (e) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148-11149.
6. (f) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204-11205.
7. (a) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
8. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142.
9. Evans, D. A.; Seidel, D. J. Am. Chem. Soc. 2005, 127, 9958-9959.
10. Complex 1b has been shown to catalyze an enantioselective alkylation, see: Evans, D. A.; Thomson, R. J. J. Am. Chem. Soc. 2005, 127, 10474-10475.
11. (a) 1,3-Diketones: Itoh, K.; Hasegawa, M.; Tanaka, J.; Kanemasa, S. Org. Lett. 2005, 7, 979-981.
12. (b) Malononitrile: Itoh, K.; Oderaotoshi, Y.; Kanemasa, S. Tetrahedron: Asymmetry 2003, 14, 635-639.
13. (c) Nitromethane: Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395.
14. (d) Thiols: Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675-8676.
15. 4.
16. Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559-7573.
17. For the synthesis of related structures, see: Katritzky, A. R.; Deniski, O. V. J. Org. Chem. 2002, 67, 3104-3108. See also ref 5a.
18. Other alkyl acetoacetates were also effective; Me: 86% ee. Et: 91% ee, Bn: 93% ee. See Supporting Information for full details.
19. (a) Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087-2088.
20. (b) Hoffman, R. V.; Saenz, J. E. Tetrahedron Lett. 1997, 38, 8469-8472.
21. 8b and 8f are known compounds and allowed the assignment of the absolute stereochemistry. See: (a) Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 45, 4967-4970.
22. (b) Shi, Y.; Wulff, W. D.; Glenn, P. A.; Rheingold, A. L. Chem. Commun. 1996, 2601-2602.
23. See Supporting Information for full details.
24. 2 by docking the thiazolidinethione to the Ni center, followed by PM3 minimization. See Supporting Information for X-ray structure.
25. An enantioselective hydrogenation of pyrone derivatives to 5,6-dihydro-2-pyrones has been reponed. See: Fehr. M. J.; Consiglio, G.; Scalone. M.; Schmid. R. J. Org. Chem. 1999, 64, 5678-5776 and references therein.
26. For a review, see: Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.2.