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Volumn 39, Issue 36, 1998, Pages 6467-6470

An efficient synthesis of (2S,3R)-3-hydroxylysine via ruthenium catalyzed asymmetric hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYLYSINE; ALPHA ACETAMIDO BETA KETOPHTALIMIDOHEXANOIC ACID; HEXANOIC ACID DERIVATIVE; LYSINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 0032171334     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01387-2     Document Type: Article
Times cited : (62)

References (30)
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    • 4. Total synthesis of (-) balanol has been achieved by four groups : a) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572-4581.
    • (1994) J. Org. Chem. , vol.59 , pp. 5147-5148
    • Lampe, J.W.1    Hughes, P.F.2    Biggers, C.K.3    Smith, S.H.4    Hu, H.5
  • 7
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    • 4. Total synthesis of (-) balanol has been achieved by four groups : a) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572-4581.
    • (1996) J. Org. Chem. , vol.61 , pp. 4572-4581
    • Lampe, J.W.1    Hughes, P.F.2    Biggers, C.K.3    Smith, S.H.4    Hu, H.5
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    • b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Nicolaou, K. C. Koide, K.; Bunnage, M. E. Chem. Eur. J. 1995, 1, 454-466.
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    • d) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 581-582. For a formal synthesis of (-) balanol, see also Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
    • (1997) Synlett , pp. 581-582
    • Miyabe, H.1    Torieda, M.2    Kiguchi, T.3    Naito, T.4
  • 12
    • 0031562447 scopus 로고    scopus 로고
    • d) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 581-582. For a formal synthesis of (-) balanol, see also Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1693-1696
    • Wu, M.H.1    Jacobsen, E.N.2
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    • 8. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. For an achiral synthesis of threo-hydroxylysine, see also Stammer, C. H.; Webb R. G. J. Org. Chem. 1969, 34, 2306-2311.
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    • 8. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. For an achiral synthesis of threo-hydroxylysine, see also Stammer, C. H.; Webb R. G. J. Org. Chem. 1969, 34, 2306-2311.
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    • note
    • 6 C,58.61; H,5.79; N,8.04. Found C,58.51; H,5.83; N,8.09. A 3:1 mixture syn+anti 9 has been obtained in reaction conditions of table 1 (entry 1) : the minor anti diastereomer shows characteristic signals at δ 4.0 ppm (m) and 6.6 ppm (bd).


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