Stereoselective synthesis of conformationally restricted analogues of aspartic and glutamic acids front endocyclic enecarbamates

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1869-1872

  Carpes, Marcos José S ^a   Miranda, Paulo Cesar M L ^a   Correia, Carlos Roque D ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ASPARTIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0031575815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00238-4     Document Type: Article

References (24)

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16. 6. Part of this work was presented at the 11th International Conference on Organic Synthesis, Amsterdam, The Netherlands, June 30-July 4, 1996 (PO-75).
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20. 10. For previous works related to the synthesis of compounds 8, 9,13 and 14 see: a) Humphrey, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467-2472;
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22. (c) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron 1995, 51, 8525-8544 and references cited therein. All spectroscopic data obtained were in very good agreement with those reported. Note: after completion of the work presented in Scheme 1 we performed the conversion of 7 into 8 and 11 into 13 using acid hydrolysis (HCl 6M) in 90% and 87% yields respectively. However, some epimerization has been observed in these cases.
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24. D= -37.2 (c 1.1, MeOH).