N-Bromoacetamide - A New Nitrogen Source for the Catalytic Asymmetric Aminohydroxylation of Olefins

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1483-1486

  Bruncko, Milan ^a   Schlingloff, Gunther ^a   Barry Sharpless, K ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amino alcohols; Asymmetric aminohydroxylation; Asymmetric catalysis; Haloamides; Homogeneous catalysis

Indexed keywords

EID: 0030799342     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199714831     Document Type: Article

References (36)

1. a) G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454;
2. a) G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454;
3. b) G. Li, K. B. Sharpless, Acta Chem. Scand. 1996, 50, 649-651;
4. 2PHAL;
5. 2PHAL;
6. d) G. Li; H. H. Angert; K. B. Sharpless, Angew. Chem. 1996, 108, 2995-2999; Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817: Corrigendum: In the Experimental Procedure in this paper the yield of pure (S)-2 should read 0.230 g and not 0.460 g.
7. d) G. Li; H. H. Angert; K. B. Sharpless, Angew. Chem. 1996, 108, 2995-2999; Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817: Corrigendum: In the Experimental Procedure in this paper the yield of pure (S)-2 should read 0.230 g and not 0.460 g.
8. a) J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420-7421;
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11. a) A. W. Hofmann, Ber. Dtsch. Chem. Ges. 1881, 14, 2725;
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13. 3/hexane 1/1) before use. We recommend preparation by a published procedure: E. P. Oliveto, C. Gerold, Organic Syntheses Collective Volume IV, 104-105. The purity of this oxidant was checked by acid-base titration: C. Bachand, H. Driguez, J. M. Paton, D. Touchard, J. Lessard, J. Org. Chem. 1974, 39, 3136-3138.
14. 3/hexane 1/1) before use. We recommend preparation by a published procedure: E. P. Oliveto, C. Gerold, Organic Syntheses Collective Volume IV, 104-105. The purity of this oxidant was checked by acid-base titration: C. Bachand, H. Driguez, J. M. Paton, D. Touchard, J. Lessard, J. Org. Chem. 1974, 39, 3136-3138.
15. b) S. C. Virgil in Encyclopedia of Reagents for Organic Synthesis, Vol. 1 (Ed. : L. A. Paquette), Wiley, New York, 1995, p. 691.
16. VIII, releasing two equivalents of base, was taken into account.
17. The use of isopropyl cinnamates instead of the methyl esters is preferable in terms of greater stability towards hydrolysis and enhanced regioselectivity under the reaction conditions. As in the case of compounds 1 and 2, which are quite soluble in the reaction medium, the use of more than 50% (v/v) water may result in slightly increased regioselectivities.
18. 2AQN are commercially available (Aldrich); an improved synthesis will be reported elsewhere.
19. 2AQN are commercially available (Aldrich); an improved synthesis will be reported elsewhere.
20. K. L. Reddy, G. Li, K. B. Sharpless, unpublished results. See also ref. [1d]. [10] Preliminary experiments with other substrates indicate that a reversal of regio-chemistry occurs when anthraquinone-derived ligands are used instead of phthalazines.
21. So far, only a few exceptions to our mnemonic device for the AD have been reported: a) K. J. Hale, S. Manaviazar, S. A. Beak, Tetrahedron Lett. 1994, 35, 425-428; b) D. J. Krysan, ibid. 1996, 37, 1375-1376; D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1996, 118, 2301-2302; P. Salvadori, S. Superchi, E Minutolo, J. Org. Chem. 1996, 61, 4190-4191; e) K. P. M. Vanhessche, K. B. Sharpless, ibid. 1996, 61, 7987-7979.
22. So far, only a few exceptions to our mnemonic device for the AD have been reported: a) K. J. Hale, S. Manaviazar, S. A. Beak, Tetrahedron Lett. 1994, 35, 425-428; b) D. J. Krysan, ibid. 1996, 37, 1375-1376; D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1996, 118, 2301-2302; P. Salvadori, S. Superchi, E Minutolo, J. Org. Chem. 1996, 61, 4190-4191; e) K. P. M. Vanhessche, K. B. Sharpless, ibid. 1996, 61, 7987-7979.
23. So far, only a few exceptions to our mnemonic device for the AD have been reported: a) K. J. Hale, S. Manaviazar, S. A. Beak, Tetrahedron Lett. 1994, 35, 425-428; b) D. J. Krysan, ibid. 1996, 37, 1375-1376; D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1996, 118, 2301-2302; P. Salvadori, S. Superchi, E Minutolo, J. Org. Chem. 1996, 61, 4190-4191; e) K. P. M. Vanhessche, K. B. Sharpless, ibid. 1996, 61, 7987-7979.
24. So far, only a few exceptions to our mnemonic device for the AD have been reported: a) K. J. Hale, S. Manaviazar, S. A. Beak, Tetrahedron Lett. 1994, 35, 425-428; b) D. J. Krysan, ibid. 1996, 37, 1375-1376; D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1996, 118, 2301-2302; P. Salvadori, S. Superchi, E Minutolo, J. Org. Chem. 1996, 61, 4190-4191; e) K. P. M. Vanhessche, K. B. Sharpless, ibid. 1996, 61, 7987-7979.
25. So far, only a few exceptions to our mnemonic device for the AD have been reported: a) K. J. Hale, S. Manaviazar, S. A. Beak, Tetrahedron Lett. 1994, 35, 425-428; b) D. J. Krysan, ibid. 1996, 37, 1375-1376; D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1996, 118, 2301-2302; P. Salvadori, S. Superchi, E Minutolo, J. Org. Chem. 1996, 61, 4190-4191; e) K. P. M. Vanhessche, K. B. Sharpless, ibid. 1996, 61, 7987-7979.
26. The yield might be further increased (5-10%) by optimizing the isolation procedure. We believe that this new amide-AA-based protocol is superior to our earlier AA- or AD-based approaches: a) Ref. [1b]; b) Z.-M. Wang, H. C. Kolb, K. B. Sharpless, J. Org. Chem. 1994, 59, 5104-5105.
27. The yield might be further increased (5-10%) by optimizing the isolation procedure. We believe that this new amide-AA-based protocol is superior to our earlier AA- or AD-based approaches: a) Ref. [1b]; b) Z.-M. Wang, H. C. Kolb, K. B. Sharpless, J. Org. Chem. 1994, 59, 5104-5105.
28. The fact that less ligand than osmium can be used, demonstrates once again the great advantages of a ligand-accelerated catalysis (LAC); for a review see D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
29. The fact that less ligand than osmium can be used, demonstrates once again the great advantages of a ligand-accelerated catalysis (LAC); for a review see D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
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35. T. Izumi, K. Fukaya, Bull. Chem. Soc. Jpn. 1993, 66, 1216-1221.
36. Prepared from (R)-2-phenylglycinol (Aldrich).