Epimerization of diastereomeric α-amino nitriles to single stereoisomers in the solid state

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2241-2244

  Sakurai, Rumiko ^a   Suzuki, Shuji ^b   Hashimoto, Junichi ^b   Baba, Manabu ^b   Itoh, Osamu ^c   Uchida, Akira ^c   Hattori, Tetsutaro ^a   Miyano, Sotaro ^a   Yamaura, Masanori ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b IWAKI MEISEI UNIVERSITY   (Japan)

^c TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; DIMETHYL SULFOXIDE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; EPIMERIZATION; ISOMERISM; REACTION ANALYSIS; ROOM TEMPERATURE; SOLID STATE; STEREOCHEMISTRY;

EID: 3142744646     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049256q     Document Type: Article

References (24)

1. Reviews: (a) Toda, F. Synlett 1993, 303. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480. (c) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (d) Toda, F. Aust. J. Chem. 2001, 54, 573.
2. Reviews: (a) Toda, F. Synlett 1993, 303. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480. (c) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (d) Toda, F. Aust. J. Chem. 2001, 54, 573.
3. Reviews: (a) Toda, F. Synlett 1993, 303. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480. (c) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (d) Toda, F. Aust. J. Chem. 2001, 54, 573.
4. Reviews: (a) Toda, F. Synlett 1993, 303. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480. (c) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (d) Toda, F. Aust. J. Chem. 2001, 54, 573.
5. Reviews: (a) Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 12, 191. (b) Sakamoto, M. Chem. Eur. J. 1997, 3, 684.
6. Reviews: (a) Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 12, 191. (b) Sakamoto, M. Chem. Eur. J. 1997, 3, 684.
7. Sakamoto, M.; Iwamoto, T.; Nono, N.; Ando, M.; Arai, W.; Mino, T.; Fujita, T. J. Org. Chem. 2003, 68, 942.
8. Wilson, K. R.; Pincock, R. E. J. Am. Chem. Soc. 1975, 97, 1474.
9. Einhorn, C.; Durif, A.; Averbuch, M.-T.; Einhorn, J. Angew. Chem., Int. Ed. 2001, 40, 1926.
10. (a) Osano, Y. T.; Uchida, A.; Ohashi, Y. Nature, 1991, 352, 510.
11. (b) Hashizume, D.; Ohashi, Y. J. Phys. Org. Chem. 2000, 13, 415.
12. For utilization of cis-1aminoindan-2-ol in asymmetric synthesis, see: Ghosh, A. K.; Fidanze, S.; Senanayake, C. H. Synthesis 1998, 937.
13. Sakurai, R.; Sakai, K. Tetrahedron: Asymmetry 2003, 14, 411.
14. Recent reviews on the asymmetric Strecker reactions: (a) Gröger, H. Chem. Rev. 2003, 103, 2795. (b) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
15. Recent reviews on the asymmetric Strecker reactions: (a) Gröger, H. Chem. Rev. 2003, 103, 2795. (b) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
16. Recent reviews on the asymmetric Strecker reactions: (a) Gröger, H. Chem. Rev. 2003, 103, 2795. (b) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
17. For utilization of amino alcohols as chiral auxiliaries for the Strecker reaction, see: (a) Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (c) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120. (d) Dave, R. H.; Hosangadi, B. D. Tetrahedron 1999, 55, 11295.
18. For utilization of amino alcohols as chiral auxiliaries for the Strecker reaction, see: (a) Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (c) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120. (d) Dave, R. H.; Hosangadi, B. D. Tetrahedron 1999, 55, 11295.
19. For utilization of amino alcohols as chiral auxiliaries for the Strecker reaction, see: (a) Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (c) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120. (d) Dave, R. H.; Hosangadi, B. D. Tetrahedron 1999, 55, 11295.
20. For utilization of amino alcohols as chiral auxiliaries for the Strecker reaction, see: (a) Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (c) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120. (d) Dave, R. H.; Hosangadi, B. D. Tetrahedron 1999, 55, 11295.
21. A crystallization-induced asymmetric transformation in the Strecker reaction has been reported: Boesten, W. H. J.; Seerden, J.-P. G.; de Lange, B.; Dielemans, H. J. A.; Eisenberg, H. L. M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 1121.
22. Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2000, 2321.
23. 3, Z = 1.
24. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.