Chiral γ-amino amide synthesis by heterobimetallic lanthanum/lithium/pybox-catalyzed direct asymmetric Mannich-type reactions of α-keto anilides

Angewandte Chemie - International Edition

Volumn 47, Issue 36, 2008, Pages 6847-6850

  Lu, Gang ^a   Morimoto, Hiroyuki ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Amino acids; Asymmetric catalysis; Asymmetric synthesis; Heterometallic complexes; Mannich reaction

Indexed keywords

AMINATION; AMINES; CHEMICAL REACTIONS; COMPLEXATION; SYNTHESIS (CHEMICAL);

AMINO ACIDS; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; HETEROMETALLIC COMPLEXES; MANNICH REACTION;

AMIDES;

(4'S,5'S) 2,6 BIS(4' (TRIISOPROPYLSILYL)OXYMETHYL 5' PHENYL 1',3' OXAZOLIN 2' YL)PYRIDINE; (4'S,5'S)-2,6-BIS(4'-(TRIISOPROPYLSILYL)OXYMETHYL-5'-PHENYL-1',3'-OXAZOLIN-2'-YL)PYRIDINE; AMIDE; ANILIDE; KETONE; LANTHANUM; LITHIUM; OXAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AMIDES; ANILIDES; CATALYSIS; KETONES; LANTHANUM; LITHIUM; OXAZOLES; PYRIDINES; STEREOISOMERISM;

EID: 52449119278     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801564     Document Type: Article

References (54)

1. For recent reviews on direct catalytic asymmetric Mannich-type reactions, see: a) J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29;
2. b) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797;
3. c) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471;
4. d) G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541;
5. e) M. M. B. Marques, Angew. Chem. 2006, 118, 356;
6. Angew. Chem. Int. Ed. 2006, 45, 348;
7. f) M. Shibasaki, S. Matsunaga, J. Organomet. Chem. 2006, 691, 2089.
8. For a review on the synthesis of glutamic acid derivatives, see: a) V. A. Soloshonok, Curr. Org. Chem. 2002, 6, 341;
9. See also reviews for the use of glycine Schiff bases as donors in asymmetric synthesis: b) T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300;
10. Angew. Chem. Int. Ed. 2007, 46, 4222;
11. c) M. O'Donnell, Acc. Chem. Res. 2004, 37, 506.
12. For reviews on asymmetric conjugate additions to nitroolefins, see: a) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877;
13. b) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
14. Angew. Chem. Int. Ed. 2007, 46, 1570, and references therein;
15. See also related reviews: c) J. Christoffers, G. Koripelly, A. Rosiak, M. Rössle, Synthesis 2007, 1279;
16. d) S. J. Connon, Chem. Eur. J. 2006, 12, 5418.
17. - followed by reduction: a) G. M. Sammis, H. Danjo, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 9928, and references therein;
18. b) T. Mita, K. Sasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 514.
19. S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973.
20. Review: M. Shibasaki, M. Kanai, N. Fukuda, Chem. Asian J. 2007, 2, 20.
21. a) J. S. Bryans, D. J. Wustrow, Med. Res. Rev. 1999, 19, 149;
22. b) J. R. Cooper, F. E. Bloom, R. H. Roth, The Biochemical Basis of Neuropharmacology; Oxford Press, Oxford, 2003;
23. c) D. M. Tassone, E. Boyce, J. Guyer, D. Nuzum, Clin. Ther. 2007, 29, 26.
24. E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2416.
25. K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083;
26. Angew. Chem. Int. Ed. 2001, 40, 2995.
27. a) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712;
28. b) T. Yoshida, H. Morimoto, N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 3536;
29. Angew. Chem. Int. Ed. 2005, 44, 3470;
30. c) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439;
31. Angew. Chem. Int. Ed. 2005, 44, 4365;
32. d) S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900;
33. e) Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 2170.
34. H. Morimoto, G. Lu, N. Aoyama, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 9588.
35. For more detailed data of optimization studies, see Supporting Information.
36. For examples of the utility of related glyoxanilides as electrophiles in catalytic enantioselective reactions, see: a) D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2006, 128, 11034;
37. b) D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2007, 129, 9606.
38. For selected recent examples of N-heteroarenesulfonyl imines in asymmetric synthesis, see: a) A. S. González, R. Gómez Arrayás, J. C. Carretero, Org. Lett. 2006, 8, 2977;
39. b) J. Esquivias, R. Gómez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2007, 129, 1480, and references therein;
40. c) S. Nakamura, H. Nakashima, H. Sugimoto, N. Shibata, T. Toru, Tetrahedron Lett. 2006, 47, 7599;
41. d) S. Nakamura, H. Nakashima, H. Sugimoto, H. Sano, M. Hattori, N. Shibata, T. Toru, Chem. Eur. J. 2008, 14, 2145, and references therein.
42. The absolute and relative configurations of 4aa, and the relative configuration of 3ha were determined by X-ray crystallographic analysis. Those of others were tentatively assigned by analogy to 3ha and 4aa. CCDC 680941 and 680942 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data_request/cif
43. 2/hexane, giving crystalline racemic-3ka and a mother liquor containing 3ka with 97% ee.
44. 0, see ref. [11] and [14].
45. For transformations of anilides into carboxylic acid, ester, amide, and alcohol under mild reaction conditions, see: a) D. A. Evans, Y. Aye, J. Wu, Org. Lett. 2006, 8, 2071;
46. b) S. Saito, S. Kobayashi, J. Am. Chem. Soc. 2006, 128, 8704;
47. c) Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, Synlett 2006, 3529, and references therein. See also ref. [13] and references therein.
48. 1 had drastic effects on stereoselectivity in the present system. Thus, we believe that the role of achiral base (LiOAr) in the present system is different from that in ref. [11].
49. For recent reviews on bimetallic cooperative asymmetric catalysis, see a) S. Matsunaga, M. Shibasaki, Bull. Chem. Soc. Jpn. 2008, 81, 60;
50. b) M. Shibasaki, M. Kanai, Org. Biomol. Chem. 2007, 5, 2027;
51. c) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269.
52. At this moment, we speculate that the present heterobimetallic La/Li/pybox system works as a bifunctional cooperative catalyst, as has been noted in other La/Li/binol-type complexes. For a review, see: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187.
53. 3/pybox complexes(RE=rare earth metal), see: b) S. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001;
54. c) J. M. Keith, E. N. Jacobsen, Org. Lett. 2004, 6, 153. An intermolecular homobimetallic cooperative mechanism was postulated in those studies.