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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.
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Dimethyl N-(PhF)aspartate was prepared as described in (a) Jamison, T. F.; Rapoport, H. Org. Synth. 1992, 71, 226.
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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.
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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.
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Manuscript in preparation
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(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.
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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:
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33744863208
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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.
-
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