Multiple component reactions: An efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of β-amino carbonyl libraries

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2143-2150

  Adrian Jr , James C ^a   Snapper, Marc L ^b  

^a UNION COLLEGE   (United States)

^b BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CONDENSATION; NICKEL;

MULTIPLE-COMPONENT CONDENSATIONS (MCC);

REACTION KINETICS;

AMIDE; BETA AMINO CARBONYL DERIVATIVE; CARBONYL DERIVATIVE; ESTER; KETONE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; METHODOLOGY; POLYMERIZATION; REACTION ANALYSIS; REFORMATSKY REACTION; SYNTHESIS;

AMINES; CARBONIC ACID; CATALYSIS; CHROMATOGRAPHY, THIN LAYER; COMBINATORIAL CHEMISTRY TECHNIQUES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NICKEL; STEREOISOMERISM;

EID: 0037459711     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026847q     Document Type: Article

References (37)

1. (a) Armstrong, W. R.; Combs, A. P.; Tempest, P. A.; Brown, D. B.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
2. For leading references, see: (b) Kobayashi, S. Curr. Opin. Chem. Biol. 2000, 4, 338-345.
3. (c) Willi, B. Methods Princ. Med. Chem. 2000, 9, 6-21.
4. Biginelli, P. Ber. Dtsch. Chem. Ges. 1891, 24, 2962.
5. Reformatsky, S. Ber. Dtsch. Chem. Ges. 1887, 20, 1210.
6. For recent reviews of the Reformatsky reaction, see: (a) Fürstner, A. Synthesis 1989, 571-590. (b) Rathke M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 277-299. (c) Fürstner, A In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: New York, 1999; pp 287-305.
7. For recent reviews of the Reformatsky reaction, see: (a) Fürstner, A. Synthesis 1989, 571-590. (b) Rathke M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 277-299. (c) Fürstner, A In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: New York, 1999; pp 287-305.
8. For recent reviews of the Reformatsky reaction, see: (a) Fürstner, A. Synthesis 1989, 571-590. (b) Rathke M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 277-299. (c) Fürstner, A In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: New York, 1999; pp 287-305.
9. (a) Inoue, S.; Imanaka, Y. J. Organomet. Chem. 1972, 35, 1-7.
10. For leading references, see: (b) Knochel, P.; Singer, R. Chem. Rev. 1993, 93, 3. 2117-2188.
11. (c) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
12. (a) Sibille, S.; d'Incam, E.; Leport, L.; Massebiau, M.-C.; Périchon J. Tetrahedron Lett. 1987, 28, 55-58.
13. (b) Mcharek, S.; Sibille, S.; Nédélec, J.-Y.; Périchon J. J. Organomet. Chem. 1991, 401, 211-215.
14. (c) Conan, A.; Sibille, S.; Périchon J. J. Org, Chem. 1991, 56, 2018-2024.
15. Ding, Y.; Zhao, G. J. Chem. Soc., Chem. Commun. 1992, 941-942.
16. Kanai, K.; Wakabayashi, H.; Honda, T Org. Lett. 2000, 2, 2549-2551.
17. Ocampo, R.; Dolbier, W. R.; Abboud, K. A.; Zuluaga, F. J. Org. Chem. 2002, 67, 72-78.
18. Gilman, H.; Speeter, M. J. Am. Chem. Soc. 1943, 65, 2255-2256.
19. Dardoize and co-workers reported that β-amino esters and lactams were formed in ratios that were temperature dependent. For leading references, see: Dardoize, F.; Moreau, J.-L.; Gaudemar, M Bull. Soc. Chim. Fr. 1972, 3841-3846.
20. Adrian, J. C., Jr.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
21. (a) Nishiyama, T.; Kishi, H.; Kitano, K.; Yamada, F. Bull. Chem. Soc. Jpn. 1994, 67, 1765-1768.
22. (b) Saidi, M. R.; Azizi, N.; Zali-Boinee, H. Tetrahedron 2001, 57, 6829-6832.
23. (c) Honda, T.; Wakabayashi, H.; Kanai, K. Chem. Pharm. Bull. 2002, 50, 307-308.
24. The β-amino carbonyl products of the multicomponent Reformatsky method reported herein are complimentary to those obtained from the Mannich reaction. For recent examples of multicomponent Mannich reactions, see: (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833. (b) Loh, T.-P.; Liung, S. B. K. W.; Tan, K.-L.; Wei, L.-L. Tetrahedron 2000, 56, 3227-3237. (c) Takaya, J.; Kagoshima, H.; Akiyama, T. Org. Lett. 2000, 2, 1577-1579. (d) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426-1428.
25. The β-amino carbonyl products of the multicomponent Reformatsky method reported herein are complimentary to those obtained from the Mannich reaction. For recent examples of multicomponent Mannich reactions, see: (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833. (b) Loh, T.-P.; Liung, S. B. K. W.; Tan, K.-L.; Wei, L.-L. Tetrahedron 2000, 56, 3227-3237. (c) Takaya, J.; Kagoshima, H.; Akiyama, T. Org. Lett. 2000, 2, 1577-1579. (d) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426-1428.
26. The β-amino carbonyl products of the multicomponent Reformatsky method reported herein are complimentary to those obtained from the Mannich reaction. For recent examples of multicomponent Mannich reactions, see: (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833. (b) Loh, T.-P.; Liung, S. B. K. W.; Tan, K.-L.; Wei, L.-L. Tetrahedron 2000, 56, 3227-3237. (c) Takaya, J.; Kagoshima, H.; Akiyama, T. Org. Lett. 2000, 2, 1577-1579. (d) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426-1428.
27. The β-amino carbonyl products of the multicomponent Reformatsky method reported herein are complimentary to those obtained from the Mannich reaction. For recent examples of multicomponent Mannich reactions, see: (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833. (b) Loh, T.-P.; Liung, S. B. K. W.; Tan, K.-L.; Wei, L.-L. Tetrahedron 2000, 56, 3227-3237. (c) Takaya, J.; Kagoshima, H.; Akiyama, T. Org. Lett. 2000, 2, 1577-1579. (d) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426-1428.
28. 1H NMR of the reaction mixture after workup.
29. In their initial paper (ref 8), Honda and co-workers specifically comment that no ethyl adducts were observed. In their subsequent paper (ref 13c), they make no comment on the formation of ethyl adducts.
30. In this initial case and in all subsequent cases, the reactions were judged to be complete based on the disappearance of the limiting aldehyde as determined by TLC. We made no attempt to determine the relative rate of formation of the ester 3a beyond following the course of the reaction by TLC.
31. We have since determined that secondary amides are also effective enolate sources. The following example has not been optimized: Equation presented
32. Nahm, S.; Weinreb, S. M.; Tetrahedron Lett. 1981, 22, 3815-3818.
33. For reviews on the growing synthetic utility of the Weinreb amide, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15-40. (b) Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem. 2000, 342, 340-347.
34. For reviews on the growing synthetic utility of the Weinreb amide, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15-40. (b) Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem. 2000, 342, 340-347.
35. The "activating" effect of an electron-withdrawing group at the ortho position of the N-phenyl group has also been observed for addition of lithium enolates to imines; see: Saito, S.; Hatanaka, K.; Yamaoto, H. Org. Lett. 2000, 2, 1891-1894.
36. 1H NMR of the reaction mixture after workup.
37. See the Supporting Information.