Multiple component approaches to C-glycosyl β-amino acids by complementary one-pot mannich-type and reformatsky-type reactions

Chemistry - A European Journal

Volumn 11, Issue 23, 2005, Pages 7110-7125

  Dondoni, Alessandro ^a   Massi, Alessandro ^a   Sabbatini, Simona ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

Amino acids glycosides; Mannich reaction; Multicomponent reactions; Reformatsky reaction

Indexed keywords

AMINO ACIDS GLYCOSIDES; MANNICH REACTION; MULTICOMPONENT REACTIONS;

CRYSTAL STRUCTURE; ESTERS; PROPANE; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS;

AMINO ACID; CATION;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; ELECTRON; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMINO ACIDS; CATIONS; ELECTRONS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR;

EID: 28044439641     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500823     Document Type: Conference Paper

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179. RS) with a regular sign distribution for all protons of 7aa.
180. The lack of any diagnostic protons in the alkyl chain part of α,α-difluoro C-glycosyl β-amino acids 19 and 20 doesn't allow for a reliable assignment of the absolute configuration at C-3 of this class of compounds by NMR.
181. R. Badorrey, C. Cativiela, M. D. Díaz-de-Villegas, J. A. Gálvez, Tetrahedron Lett. 2003, 44, 9189-9192.
182. a) M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204;
183. b) N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61-70
184. for an additional discussion of this model, see: c) E. L. Eliel, in Asymmetric Synthesis, Vol. 2 (Ed.: J. D. Morrison), Academic Press, New York, 1983, pp. 125-155.
185. a) N. T. Anh, Top. Curr. Chem. 1980, 88, 145-162.
186. For theoretical studies which support the polar Felkin-Anh model, see: b) Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1987, 109, 908-910;
187. c) G. Frenking, K. F. Köhler, M. T. Reetz, Tetrahedron 1993, 49, 3983-3984;
188. d) N. T. Anh, F. Maurel, J.-M. Lefour, New J. Chem. 1995, 19, 353-364.