Diastereo- and enantioselective allylation of substituted nitroalkanes [3]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6291-6292

  Trost, Barry M ^a   Surivet, Jean Philippe ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROMETHANE; NITROMETHANE;

CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOMER; LETTER; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0034608928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001062s     Document Type: Letter

References (30)

1. Coombes, R. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 303-382. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, I. Rosini, G.; Ballini, R. Synthesis 1988, 833. Patai, S., Ed. The Chemistry of Amino, Nitro and Related Groups; John Wiley & Sons: Chichester, 1996.
2. Coombes, R. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 303-382. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1. Rosini, G.; Ballini, R. Synthesis 1988, 833. Patai, S., Ed. The Chemistry of Amino, Nitro and Related Groups; John Wiley & Sons: Chichester, 1996.
3. Coombes, R. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 303-382. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1. Rosini, G.; Ballini, R. Synthesis 1988, 833. Patai, S., Ed. The Chemistry of Amino, Nitro and Related Groups; John Wiley & Sons: Chichester, 1996.
4. Coombes, R. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 303-382. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1. Rosini, G.; Ballini, R. Synthesis 1988, 833. Patai, S., Ed. The Chemistry of Amino, Nitro and Related Groups; John Wiley & Sons: Chichester, 1996.
5. (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418.
6. (b) Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855.
7. (c) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
8. For other types of asymmetric reactions of nitroalkanes, see: Vogel, E. M.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 1510.
9. Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Susar, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557.
10. (a) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
11. (b) Also see: Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1988, 36, 4543.
12. For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
13. For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
14. For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
15. (5) For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
16. (5) For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
17. For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
18. For achiral reactions, see: Aleksandrowicz, P.; Piotrowska, H.; Sao, W. Tetrahedron 1982, 38, 1321. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365. Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379. Ognyanov, V. I.; Hesse, M. Synthesis 1985, 645. Genêt, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. Tsuji, J.; Yamada, T.; Minami, I.; Yahara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52. 2988. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
19. Cf.: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
20. Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, F. Chem. Pharm. Bull. 1989, 37, 545. Also see: Torno, J.; Harp, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 5296. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetraheron Lett. 1981, 22, 1705. Tanner, D. D.; Balckburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557.
21. Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, F. Chem. Pharm. Bull. 1989, 37, 545. Also see: Torno, J.; Harp, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 5296. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetraheron Lett. 1981, 22, 1705. Tanner, D. D.; Balckburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557.
22. Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, F. Chem. Pharm. Bull. 1989, 37, 545. Also see: Torno, J.; Harp, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 5296. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetraheron Lett. 1981, 22, 1705. Tanner, D. D.; Balckburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557.
23. Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, F. Chem. Pharm. Bull. 1989, 37, 545. Also see: Torno, J.; Harp, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 5296. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetraheron Lett. 1981, 22, 1705. Tanner, D. D.; Balckburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557.
24. Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, F. Chem. Pharm. Bull. 1989, 37, 545. Also see: Torno, J.; Harp, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 5296. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetraheron Lett. 1981, 22, 1705. Tanner, D. D.; Balckburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557.
25. Trost, B. M.; Dietsche, T. J. J. Am. Chem. Soc. 1973, 95, 8200.
26. All new compounds have been satisfactorily characterized spectrally and their elemental compositions established by high-resolution mass spectrometry and/or combustion analysis.
27. Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4203.
28. Good diastereoselectivity has sometimes been observed in the asymmetric Henry reaction (see refs 2b,c), although it has not been rigorously established whether this is a kinetic or thermodynamic effect.
29. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235. For other studies on this effect, see: Butts, C. P.; Crosby, J.; Lloyd-Jones, G. C.; Stephan. S. C. Chem. Commun. 1999, 1707.
30. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235. For other studies on this effect, see: Butts, C. P.; Crosby, J.; Lloyd-Jones, G. C.; Stephan. S. C. Chem. Commun. 1999, 1707.