Corrigendum to: Asymmetric Amplification in the Amino Acid-Catalyzed Synthesis of Amino Acid Derivatives (Advanced Synthesis & Catalysis, (2007), 349, 11-12, (1868-1872), 10.1002/adsc.200700110);Asymmetric amplification in the amino acid-catalyzed synthesis of amino acid derivatives

Advanced Synthesis and Catalysis

Volumn 349, Issue 11-12, 2007, Pages 1868-1872

  Ibrahem, Ismail ^a   Sundén, Henrik ^a   Dziedzic, Pawel ^a   Rios, Ramon ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Amino acids; Asymmetric amplification; Homochirality; Kinetic resolution; kinetic resolution; asymmetric amplification; amino acids; homochirality

Indexed keywords

EID: 34548394458     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200890003     Document Type: Erratum

References (47)

1. a) W. A. Bonner, Orig. Life Evol. Biosphere 1991, 21, 59;
2. b) J. L. Bada, Nature 1995, 374, 594;
3. c) S. F. Mason, Nature 1985, 314, 400.
4. F. C. Frank, Biochem. Biophys. Acta 1953, 11, 459.
5. K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767;
6. T. Shibata, H. Morioka, T. Hayase, K. Choji, K. Soai, J. Am. Chem. Soc. 1996, 118, 471;
7. T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai, K. Soai, J. Am. Chem. Soc. 1998, 120, 12157;
8. K. Soai, I. Sato, Enantiomer 2001, 6, 189.
9. For original work on non-linear effect in proline-catalyzed reactions see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 1986, 108, 2353;
10. see also: b) L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 2003, 125, 16.
11. a) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975;
12. b) S. P. Mathew, H. Iwamura, D. Blackmond, Angew. Chem. Int. Ed. 2004, 43, 3317;
13. c) H. Iwamura, S. P. Mathew, D. Blackmond, J. Am. Chem. Soc. 2004, 126, 11770;
14. d) A. Córdova, M. Engqvist, I. Ibrahem, J. Casas, H. Sundén, Chem. Commun. 2005, 2047;
15. e) A. Córdova, H. Sundén, Y. Xu, I. Ibrahem, W. Zou, M. Engqvist, Chem. Eur. J. 2006, 12, 5446.
16. a) Y. Hayashi, M. Matsuzuwa, J. Yamaguchi, S. Yonehara, Y. Matsumoto, M. Shoji, D. Hashizume, H. Koshino, Angew. Chem. Int. Ed. 2006, 45, 4593;
17. b) M. Klussmann, H. Iwamura, S. P. Mathew, D. H. Wells, Jr., U. Pandya, A. Armstrong, D. G. Blackmond, Nature 2006, 441, 621;
18. c)M. Klussmann, A. J. P. White, A. Armstrong, D. G. Blackmond, Angew. Chem. Int. Ed. 2006, 45, 7985;
19. d) A. Córdova, W. Zou, P. Dziedzic, I. Ibrahem, E. Reyes, Y. Xu, Chem. Eur. J. 2006, 12, 5383; corrigendum: A. Córdova, W. Zou, P. Dziedzic, I. Ibrahem, E. Reyes, Y. Xu, Chem. Eur. J. 2006, 12, 5175;
20. e) R. Breslow, M. S. Levine, Proc. Nat. Acad. Sci. U. S. A. 2004, 103, 12979.
21. a) C. Mannich, W. Krösche, Arch. Pharm. 1912, 250, 647;
22. for selected reviews, see: b) E. F. Kleinmann, in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Flemming), Pergamon Press, New York, 1991, Vol. 2, Chapter 4.1;
23. c) M. Arend, B. Westerman, N. Risch, Angew. Chem. Int. Ed. 1998, 37, 1044;
24. d) S. Denmark, O. J.-C. Nicaise, in: Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamomoto), Springer, Berlin, 1999, Vol. 2, 93;
25. e) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069;
26. f) A. Córdova, Acc Chem. Res. 2004, 37, 102.
27. For selected examples, see: a) S. Matsunaga, N. Kumagai, N. Harada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712;
28. b) B. M. Trost, L. M. Terrell, J. Am. Chem. Soc. 2003, 125, 338;
29. c) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. Int. Ed. 2001, 40, 2995;
30. for selected organocatalytic examples see: d) A. Córdova, S.-i. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866;
31. e) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842;
32. f) A. Munch, B. Wendt, M. Christmann, Synlett 2004, 2751;
33. g) S. Fustero, D. Jimenez, J. F. Sanz-Cervera, M. Sanchez-Rosello, E. Esteban, A. Simon-Fuentes, Org. Lett. 2005, 7, 3433;
34. h) B. Westermann, C. Neuhaus, Angew. Chem. Int. Ed. 2005, 44, 4077;
35. i) I. Ibrahem, A. Córdova, Tetrahedron Lett. 2005, 46, 3363;
36. j) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. Int. Ed. 2005, 44, 4079;
37. k) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558;
38. l) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84;
39. m) I. Ibrahem, W. Zou, M. Engqvist, Y. Xu, A. Córdova, Chem. Eur. J. 2005, 11, 7024;
40. n) A. Córdova, Chem. Eur. J. 2004, 10, 1987.
41. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
42. b) S. Bahmanyar, K. N. Houk, Org. Lett. 2003, 5, 1249.
43. D. Seebach, A. K. Beck, D. M. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, W. Prikoszovich, B. Linder, Helv. Chem. Acta 2007, 90, 425.
44. We also found the oxazolidinone intermediate formed by reaction between the dimer of propionaldehyde, which is formed by the parallel dimerization of propionaldehyde, and the proline catalyst. This intermediate can also contribute to the kinetic resolution of the amino acid catalyst.
45. This behaviour was recently reported by Blackmond and co-workers see: M. Klussmann, S. P. Mathew, H. Iwamura, D. H. Wells, Jr., A. Armstrong, D. G. Blackmond, Angew. Chem. Int. Ed. 2006, 45, 7989.
46. Most recently, Mauksch, Tsogoeva and co-workers reported that the amino acid derivative formed from the proline-catalyzed reaction between acetone and imine 2 can catalyze its own formation. The reaction exhibits no non-linear effects: M. Mauksch, S. B. Tsogoeva, I. M. Martynova, S. Wei, Angew. Chem. Int. Ed. 2007, 46, 393.
47. [3] but rather an "asymmetric autocatalysis" without asymmetric amplification. For a similar example involving metals, see: K. Soai, S. Niwa, H. Hori, J. Chem. Soc., Chem. Commun. 1990, 982.