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Volumn 47, Issue 10, 2008, Pages 1871-1874

Tripeptides as efficient asymmetric catalysts for 1,4-addition reactions of aldehydes to nitroolefins - A rational approach

Author keywords

Asymmetric synthesis; Conjugate additions; Organocatalysis; Peptides

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; CHEMICAL REACTIONS; ORGANIC COMPOUNDS;

EID: 41949119312     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704972     Document Type: Article
Times cited : (244)

References (73)
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    • For examples of peptides catalyzing conjugate addition reactions see: a) S. B. Tsogoeva, S. B. Jagtap, Z. A. Ardemasova, Tetrahedron: Asymmetry 2006, 17, 989-992;
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    • For additions of carbonyl compounds to nitroolefins catalyzed by proline see: a
    • For additions of carbonyl compounds to nitroolefins catalyzed by proline see: a) B. M. Choudary, C. V. Rajasekhar, G. G. Krishma, K. R. Reddy, Synth. Commun. 2007, 37, 91-98;
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    • For examples of conjugate additions between aldehydes and nitroolefins catalyzed by organocatalysts see: a) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602;
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    • Experiments with peptides bearing a protected secondary amine or a protected carboxylic acid were either not catalytically active or showed significantly poorer catalytic properties; see the Supporting Information
    • Experiments with peptides bearing a protected secondary amine or a protected carboxylic acid were either not catalytically active or showed significantly poorer catalytic properties; see the Supporting Information.
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    • For examples of the use of 5 mol% of catalyst and efficient catalysis with aliphatic aldehydes see reference [10
    • For examples of the use of 5 mol% of catalyst and efficient catalysis with aliphatic aldehydes see reference [10].
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    • Peptides 1 and 4 can be easily prepared on a 10-g scale within a day by standard solid-phase synthesis using the Fmoc/tBu protocol for peptide synthesis.
    • Peptides 1 and 4 can be easily prepared on a 10-g scale within a day by standard solid-phase synthesis using the Fmoc/tBu protocol for peptide synthesis.
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    • Calculations were performed by using the OPLS-AA force field
    • Calculations were performed by using the OPLS-AA force field: W. L. Jorgensen, D. S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc. 1996, 118, 11225-11236.
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    • Jorgensen, W.L.1    Maxwell, D.S.2    Tirado-Rives, J.3
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    • Molecular modelling studies with peptides 2 and 3 revealed lowest energy conformations similar to that of peptide 1, thereby accounting for their respective stereoselectivities, see the Supporting Information.
    • Molecular modelling studies with peptides 2 and 3 revealed lowest energy conformations similar to that of peptide 1, thereby accounting for their respective stereoselectivities, see the Supporting Information.
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    • While this manuscript was in press, an excellent article by Ma and co-workers appeared on the title reaction. See: S. Zhu, S. Yu, D. Ma, Angew. Chem. Int. Ed. 2008, 47, 545-548
    • While this manuscript was in press, an excellent article by Ma and co-workers appeared on the title reaction. See: S. Zhu, S. Yu, D. Ma, Angew. Chem. Int. Ed. 2008, 47, 545-548.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.