Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: Improved reactivity and stereochemical outcome

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4265-4269

  Soloshonok, Vadim A ^a   Cai, Chaozhong ^a   Hruby, Victor J ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE; NICKEL COMPLEX; OXAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033402142     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00483-8     Document Type: Article

References (21)

1. (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031.
2. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045.
3. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 2, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
4. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 2, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
5. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 2, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
6. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 2, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
7. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 2, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
8. Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875.
9. Schöllkopf, U.; Pettig, D.; Busse, U. Synthesis 1986, 737.
10. For reviews, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, pp. 803-861. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (e) Hruby, V. J. Med. Res. Rev. 1989, 9, 343.
11. For reviews, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, pp. 803-861. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (e) Hruby, V. J. Med. Res. Rev. 1989, 9, 343.
12. For reviews, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, pp. 803-861. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (e) Hruby, V. J. Med. Res. Rev. 1989, 9, 343.
13. For reviews, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, pp. 803-861. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (e) Hruby, V. J. Med. Res. Rev. 1989, 9, 343.
14. For reviews, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, pp. 803-861. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (e) Hruby, V. J. Med. Res. Rev. 1989, 9, 343.
15. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Sons: Chichester, 1999.
16. Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 1999, 41, 135.
17. In the reaction of complex 1 with ethyl crotonate, the main (2S,3S)-diastereomer was isolated in 53% yield by crystallizing the resultant mixture of three diastereomeric products; see Ref. 2a.
18. Soloshonok, V. A.; Cai, C.; Hruby, V. J., unpublished data.
19. The absolute configuration of the products was unambiguously assigned on the basis of chiroptical and spectral properties of the corresponding Ni(II)-complexes as well as by comparison of chiroptical and spectral data of the isolated pyroglutamic acids with the literature data; see Ref. 2 and literature cited therein.
20. The (2S,3R)-configuration, a consequence of the Cahn-Ingold-Prelog priority, is stereochemically equivalent to the (2S,3S)-configuration in the aliphatic series: Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
21. 2O:EtOH (2:1). The acidic fraction which emerged from the column was collected and evaporated to afford (2R,3S)-3-phenylpyroglutamic acid 6d (0.40 g, 85% yield). The product was recrystallized from THF/hexanes to give an analytically pure sample of 6d.