Evaluation of the relationship between the catalyst structure and regio- as well as stereoselectivity in the chiral ammonium bifluoride-catalyzed asymmetric addition of silyl nitronates to α,β-unsaturated aldehydes

Chemistry Letters

Volumn 33, Issue 7, 2004, Pages 824-825

  Ooi, Takashi ^a   Morimoto, Kumiko ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMMONIUM DERIVATIVE; AMMONIUM HYDROGEN FLUORIDE; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; EVALUATION; STEREOCHEMISTRY;

EID: 4143132216     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.824     Document Type: Article

References (22)

1. T. Ooi, K. Doda, and K. Maruoka, J. Am. Chem. Soc., 125, 9022 (2003).
2. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
3. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
4. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
5. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
6. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
7. For limited examples of catalytic asymmetric Michael addition to α,β-unsaturated aldehydes, see: a) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem., Int. Ed. Engl., 32, 1176 (1993). b) M. Yamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 61, 3520 (1996). c) M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun., 2000, 1851. d) M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron, 56, 9589 (2000). e) G. Kumaraswamy, M. N. V. Sastry, and N. Jena, Tetrahedron Lett., 42, 8515 (2001). f) S. P. Brown, N. C. Goodwin, and D. W. C. MacMillan, J. Am. Chem. Soc., 125, 1192 (2003).
8. For the preparation of silyl nitronates, see, for example: D. Seebach, A. K. Beck, T. Mukhopadhyay, and E. Thomas, Helv. Chim. Acta, 65, 1101 (1982).
9. For the synthesis and utility of this type of chiral ammonium bromide, see: T. Ooi, M. Kameda, and K. Maruoka, J. Am. Chem. Soc., 125, 5139 (2003).
10. To clearly extract the effect of the catalyst structure on the regio- and stereoselectivity, we decided to use THF as solvent throughout this work.
11. T. Ooi, M. Takahashi, K. Doda, and K. Maruoka, J. Am. Chem. Soc., 124, 7640 (2002).
12. a) T. Ooi, K. Doda, and K. Maruoka, Org. Lett., 3, 1273 (2001).
13. b) T. Ooi, M. Taniguchi, M. Kameda, and K. Maruoka, Angew. Chem., Int. Ed., 41, 4542 (2002).
14. c) T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, and K. Maruoka, Angew. Chem., Int. Ed., 42, 3796 (2003).
15. T. Ooi, Y. Uematsu, and K. Maruoka, J. Org. Chem., 68, 4576 (2003).
16. a) T. Ooi, E. Tayama, and K. Maruoka, Angew. Chem., Int. Ed., 42, 579 (2003).
17. b) T. Ooi, D. Sakai, M. Takeuchi, and K. Maruoka, Angew. Chem., Int. Ed., 42, 5868 (2003).
18. For recent reviews on the catalytic asymmetric Michael reaction, see: a) N. Krause and A. Hoffman-Röder, Synthesis, 2001, 171. b) M. Sibi and S. Manyem, Tetrahedron, 56, 8033 (2000). c) M. Kanai and M. Shibasaki, in "Catalytic Asymmetric Synthesis," 2nd ed., ed. by I. Ojima, Wiley, New York (2000), p 569. d) K. Tomioka and Y. Nagaoka, in "Comprehensive Asymmetric Catalysis," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer-Verlag, Heidelberg (1999), Vol. III, Chap. 31.1.
19. For recent reviews on the catalytic asymmetric Michael reaction, see: a) N. Krause and A. Hoffman-Röder, Synthesis, 2001, 171. b) M. Sibi and S. Manyem, Tetrahedron, 56, 8033 (2000). c) M. Kanai and M. Shibasaki, in "Catalytic Asymmetric Synthesis," 2nd ed., ed. by I. Ojima, Wiley, New York (2000), p 569. d) K. Tomioka and Y. Nagaoka, in "Comprehensive Asymmetric Catalysis," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer-Verlag, Heidelberg (1999), Vol. III, Chap. 31.1.
20. For recent reviews on the catalytic asymmetric Michael reaction, see: a) N. Krause and A. Hoffman-Röder, Synthesis, 2001, 171. b) M. Sibi and S. Manyem, Tetrahedron, 56, 8033 (2000). c) M. Kanai and M. Shibasaki, in "Catalytic Asymmetric Synthesis," 2nd ed., ed. by I. Ojima, Wiley, New York (2000), p 569. d) K. Tomioka and Y. Nagaoka, in "Comprehensive Asymmetric Catalysis," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer-Verlag, Heidelberg (1999), Vol. III, Chap. 31.1.
21. For recent reviews on the catalytic asymmetric Michael reaction, see: a) N. Krause and A. Hoffman-Röder, Synthesis, 2001, 171. b) M. Sibi and S. Manyem, Tetrahedron, 56, 8033 (2000). c) M. Kanai and M. Shibasaki, in "Catalytic Asymmetric Synthesis," 2nd ed., ed. by I. Ojima, Wiley, New York (2000), p 569. d) K. Tomioka and Y. Nagaoka, in "Comprehensive Asymmetric Catalysis," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer-Verlag, Heidelberg (1999), Vol. III, Chap. 31.1.
22. 1 = 0.034.