Chiral Lewis acid-Hydroxylamine Hybrid Reagent for enantioselective Michael addition reaction directed towards β-amino acids synthesis

Synlett

Volumn , Issue 11, 1998, Pages 1291-1293

  Ishikawa, Teruhiko ^a   Nagai, Keita ^a   Kudoh, Takayuki ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844473152     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1929     Document Type: Article

References (26)

1. For a recent review, see Cole, D. C. Tetrahedron 1994, 50, 9517.
2. (a) Davies, S. G.; Ichihara, O.; Walters, I. A. S. Synlett 1993, 461;
3. (b) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1, 1994, 2385;
4. (c) Rico, C. J.; Dindmark, R. J.; Rogers, T. E.; Boby, P. R. J. Org. Chem. 1993, 58, 7948;
5. (d) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1992, 57, 2114;
6. (e) Enders, D.; Wahl, F.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455; for enantio-selective synthesis of β-amino acids from β-amino-α,β-unsaturated esters based on catalytic hydrogenation with chiral metal complexes,
7. see Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543 and references cited therein.
8. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1995, 1171: the reaction of methyl crotonate with (S)-MBHA has been reported so far from two laboratories:
9. see Baldwin, J. E.; Harwood, L. M.; Lombard, M. J. Tetrahedron, 1984, 40, 4363
10. (43% de) and Baldwin, S. E.; Aubé, J. Tetrahedron Lett. 1987, 28, 179 (60% de). Asymmetric syntheses of β-amino acid precursors using O-benzylhydroxylamine as a nucleophile have recently been developed:
11. Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848 (substrate control);
12. Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615 (chiral Lewis acid catalysis).
13. For the double stereo differentiation, see Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
14. The compound [(S)-5] developed by Enders is the first example of a chiral amine nucleophile in which the chiral auxiliary moiety is removable and recyclable. For this purpose, however, two chemical events after the conjugate addition have to be done and the yields of β-amino acids are rather low (16-58%).
15. Isoxazolidinone represents one of the N,O-protected form of β-amino acids.
16. The alkoxy moiety of 14 comes from optically pure pantolactone in the hope of obtaining optically active product. However, the product turned out to be 5% ee at most.
17. 13C-NMR as well, suggesting the occurrence of random association and disproportionation.
18. For chiral diols involved in these reagents, see Narasaka, K.; Iwasawa, I.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340 (for a),
19. Seebach, D.; Beck, A. K.; Imwinkelried, R.; Roggo, S.; Wonnacott, A. Helv. Chim. Acta 1987, 70, 954 (for b),
20. Jacques, J.; Fouquey, C. Org. Syn. 1988, 67, 1 and
21. Truesdale, L. K. Org. Syn. ibid. 1988, 67, 13 (for d),
22. and Maruoka, K.; Itoh, T.; Shirasaka, H.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310
23. 3MgBr.
24. 2. Since the optical rotation values of methyl (3S)-3-(N-benzoyl)aminobutanoate (Estermann, H.; Seebach, D. Helv. Chim. Acta 1988, 71, 1824) and (3R)-4-Phenyl-3-(N-tert-butoxycarbonyl)aminobutanoic acid
25. (Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165) are known, 8a and 8b were able to be correlated with these compounds. The absolute configuration of 8c, however, was merely estimated on the analogy of the relationship between the absolute structure and sign of rotation of 8a and 8b. It turned out that the absolute configuration of 8b obtained from 16d of (Z)-geometry was the same as that obtained from the (E)-isomer 16b with a preference for R-configuration.
26. For this discussion, see Noyori, R., Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994, pp 47-49.