A concise approach to structurally diverse β-amino acids

Journal of the American Chemical Society

Volumn 125, Issue 23, 2003, Pages 6846-6847

  Minter, Aaron R ^a   Fuller, Amelia A ^a   Mapp, Anna K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

AMINO ACIDS; ISOXAZOLES; STEREOISOMERISM;

EID: 0038277055     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0298747     Document Type: Article

References (33)

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2. Recent reviews on β-amino acids applications: (a) Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M. I. Curr. Med. Chem. 2002, 9, 811-822. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011. (c) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232. (e) Gademann, K.; Hintermann, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905-925. (f) Juaristi, E., Ed. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997. (g) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
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6. Recent reviews on β-amino acids applications: (a) Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M. I. Curr. Med. Chem. 2002, 9, 811-822. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011. (c) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232. (e) Gademann, K.; Hintermann, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905-925. (f) Juaristi, E., Ed. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997. (g) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
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16. 2 are sterically dissimilar, see: (a) Tang, T. P.: Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832. (b) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13. (c) Kobayashi, K.: Matoba, T.; lrisawa, S.; Takanohashi, A.; Tanmatsu, M.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2000, 73, 2805-2809. (d) Ishitani, H.; Ueno, M.; Kobayashi. S. J. Am. Chem. Soc. 2000, 122, 8180-8186.
17. 2 are sterically dissimilar, see: (a) Tang, T. P.: Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832. (b) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13. (c) Kobayashi, K.: Matoba, T.; lrisawa, S.; Takanohashi, A.; Tanmatsu, M.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2000, 73, 2805-2809. (d) Ishitani, H.; Ueno, M.; Kobayashi. S. J. Am. Chem. Soc. 2000, 122, 8180-8186.
18. 2 are sterically dissimilar, see: (a) Tang, T. P.: Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832. (b) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13. (c) Kobayashi, K.: Matoba, T.; lrisawa, S.; Takanohashi, A.; Tanmatsu, M.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2000, 73, 2805-2809. (d) Ishitani, H.; Ueno, M.; Kobayashi. S. J. Am. Chem. Soc. 2000, 122, 8180-8186.
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24. Good selectivity has only been observed when steric hindrance is also a contributing factor: (a) Jäger, V.; Buss, V.; Schwab, W. Tetrahedron Lett. 1978, 3133-3136. (b) Jäger, V.; Müller, I.; Paulus, E. F. Tetrahedron Lett. 1985, 26, 2997-3000. (c) Jäger, V.; Schwab, W.; Buss, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 601-603.
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32. 13a was subjected to reductive ozonolysis to introduce a hydroxyethyl side chain in 77% yield, for example. See the Supporting Information for details.
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