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Volumn 63, Issue 21, 1998, Pages 7463-7471

An olefination entry for the synthesis of enantiopure α,ω-diaminodicarboxylates and azabicyclo[X.Y.0]alkane amino acids

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000523948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9814602     Document Type: Article
Times cited : (70)

References (61)
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    • (e) Takahata, H.; Momose, T. In The Alkaloids Cordell, G. A., Ed. Acad. Press: New York, 1993; Vol. 44, pp 189-256.
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    • Reviewed in Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. We have adopted the nomenclature and ring system numbering used in this reference in order to maintain clarity and consistency when comparing these different heterocyclic systems.
    • (1997) Tetrahedron , vol.53 , pp. 12789
    • Hanessian, S.1    McNaughton-Smith, G.2    Lombart, H.-G.3    Lubell, W.D.4
  • 11
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    • Dimethyl N-(PhF)aspartate was prepared as described in (a) Jamison, T. F.; Rapoport, H. Org. Synth. 1992, 71, 226.
    • (1992) Org. Synth. , vol.71 , pp. 226
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  • 13
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    • Dimethyl N-(PhF)gIutamate and α-terf-butyl γ-methyl N-(PhF)glutamate were prepared as described in ref 3 above, (a) Paz, M. M.; Sardina, J. J. Org. Chem. 1993, 58, 6990.
    • (1993) J. Org. Chem. , vol.58 , pp. 6990
    • Paz, M.M.1    Sardina, J.2
  • 16
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    • Syntheses of optically active α-aminoadipate are reviewed in Pham, T.; Lubell, W. D. J. Org. Chem. 1994,59,3676 and ref 3 therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 3676
    • Pham, T.1    Lubell, W.D.2
  • 17
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    • tert -Butyl esterification using O-tert-butyl trichloroacetimidate was conducted as described in the Experimental Section. This procedure was modified from ref 3 above using O-tert-butyl trichloroacetimidate that was synthesized as described in Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans, 1 1985, 2247.
    • (1985) J. Chem. Soc., Perkin Trans, 1 , pp. 2247
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  • 18
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    • Manuscript in preparation
    • (a) Direct conversion of α-tert-butyl β-methyl N-(PhF)aspartate (3) into N-(PhF)aspartate β-aldehyde 5 with DIBAL-H has also been accomplished: Swarbrick, M. E.; Gosselin, F.; Lubell, W. D. Manuscript in preparation.
    • Swarbrick, M.E.1    Gosselin, F.2    Lubell, W.D.3
  • 20
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    • 4-LiI in THF under conditions described in Benz, G. Liebigs Ann. Chem. 1984, 1424.
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  • 25
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    • (a) α-tert-Butyl N-(BOC)aspartate β-aldehyde has been used in Wittig condensations to prepare α-aminoadipic acid: see ref 8 and Ramsamy, K.; Olsen, R. K.; Emery, T. Synthesis 1982, 42; α-aminosuberic acid:
    • (1982) Synthesis , pp. 42
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  • 26
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    • (b) Wernic, D.; DiMaio, J.; Adams, J. J. Org. Chem. 1989, 54, 4224. Alternative examples of aspartate semialdehyde include: α-tert-butyl N-(BOC)aspartate β-aldehyde
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  • 36
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    • and ref 3 therein. 2,7-Diaminosuberic acids
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    • (1992) J. Org. Chem. , vol.57 , pp. 6519
    • Williams, R.M.1    Yuan, C.2
  • 42
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    • 2 to dimethyl (2S)-N-(PhF)-3,4-didehydroglutamate has given good yield of the corresponding β-methylglutamate: see ref 7a above.
    • (1992) Chem. Rev. , vol.92 , pp. 771
    • Rossiter, B.E.1    Swingle, N.M.2
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    • note
    • 2 = 0.0728 for all data; GOF = 1.010. The author has deposited the atomic coordinates for the structure of 31 with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.