Synthesis of chiral 1,4-dihydropyridines by diastereoface-selective asymmetric addition to nicotinic amides

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4231-4234

  Yamada, Shinji ^a   Ichikawa, Mayumi ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Neighboring group effects; Pyridine; Pyridinium salts

Indexed keywords

1,4 DIHYDROPYRIDINE; AMIDE; OXAZOLIDINONE DERIVATIVE; PYRIDINIUM DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0033612176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00683-8     Document Type: Article

References (19)

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17. 2 using the SHELXL-93. Non-hydrogen atoms were refined anisotropically by full-matrix least squares method. All the H atoms were treated isotropic. The R and Rw factors after refinement of 263 parameters using 1708 observed reflections [l > 2σ(l)] were 0.0620 and 0.2441, respectively.
18. PM3 calculations were performed by using CS MOPAC Pro with MMOK empirical amide correction factor.
19. ΔδH (ppm) values of 1a: H2; 0.20, H4; 0.20, H5; 0.04, H6; 0.08. ΔδH (ppm) values of N,N-dimethylnicotinamide: H2; 0.17, H4; 0.42, H5; 0.39, H6; 0.19.