Diastereoselective synthesis of α,α-disubstituted γ-carboxypyroglutamates via Sm(III)-azomethine ylide cycloadditions

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 479-484

  Alvarez Ibarra, Carlos ^a   Csàkÿ, Aurelio G ^a   De Silanes, Isabel López ^a   Quiroga, M Luz ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PYROGLUTAMIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031025224     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961418b     Document Type: Article

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63. For the preparation of Sm(HMDS)3 from SmCl3 and NaHMDS see: Bradley, D. C.; Ghotra, J. S.; Hart, F. A. J. Chem. Soc., Dalton Trans. 1973, 1021. For the generation of ketone Sm(III)-enolates with Sm(HMDS)3 see: Sasai, H.; Arai, S.; Shibasaki, M. J. Org. Chem. 1994, 59, 2661. This base could be not strong enough for ester deprotonation. For a comparison of LDA and Li(HMDS) in ester deprotonation see: Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1992, 114, 348.
64. For the preparation of Sm(HMDS)3 from SmCl3 and NaHMDS see: Bradley, D. C.; Ghotra, J. S.; Hart, F. A. J. Chem. Soc., Dalton Trans. 1973, 1021. For the generation of ketone Sm(III)-enolates with Sm(HMDS)3 see: Sasai, H.; Arai, S.; Shibasaki, M. J. Org. Chem. 1994, 59, 2661. This base could be not strong enough for ester deprotonation. For a comparison of LDA and Li(HMDS) in ester deprotonation see: Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1992, 114, 348.
65. For the preparation of Sm(HMDS)3 from SmCl3 and NaHMDS see: Bradley, D. C.; Ghotra, J. S.; Hart, F. A. J. Chem. Soc., Dalton Trans. 1973, 1021. For the generation of ketone Sm(III)-enolates with Sm(HMDS)3 see: Sasai, H.; Arai, S.; Shibasaki, M. J. Org. Chem. 1994, 59, 2661. This base could be not strong enough for ester deprotonation. For a comparison of LDA and Li(HMDS) in ester deprotonation see: Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1992, 114, 348.
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67. 3J = 7 Hz).
68. 3-C4-C1′-H torsional angle followed by an AM1 minimization with the Polak-Ribiere conjugated gradient up to a gradient root mean square <0.1 kcal/A mol. The minimum energy conformers thus obtained for 8a and 8b differred by more than 2 kcal from their next minimum energy conformation.
69. 3-C4-C1′-H torsional angle followed by an AM1 minimization with the Polak-Ribiere conjugated gradient up to a gradient root mean square <0.1 kcal/A mol. The minimum energy conformers thus obtained for 8a and 8b differred by more than 2 kcal from their next minimum energy conformation.
70. 3-C4-C1′-H torsional angle followed by an AM1 minimization with the Polak-Ribiere conjugated gradient up to a gradient root mean square <0.1 kcal/A mol. The minimum energy conformers thus obtained for 8a and 8b differred by more than 2 kcal from their next minimum energy conformation.
71. 3-C4-C1′-H torsional angle followed by an AM1 minimization with the Polak-Ribiere conjugated gradient up to a gradient root mean square <0.1 kcal/A mol. The minimum energy conformers thus obtained for 8a and 8b differred by more than 2 kcal from their next minimum energy conformation.
72. Chelation between carbonyl groups and Sm(III) has been advanced as an important elements in the stereochemical control of ketyl radical additions. See ref 28 and references cited therein.