Chiral recognition of 1,1'-bi-2-naphthol enantiomers by twisted amidine derivatives: Rational design of a highly enantioselective receptor

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2985-2988

  Dobashi, Yasuo ^a   Kobayashi, Kiyotaka ^a   Sato, Norihisa ^a   Dobashi, Akira ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; AMIDINE; CADMIUM CHLORIDE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; STOICHIOMETRY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0032493036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00436-5     Document Type: Article

References (16)

1. 1. For example, see: (a) Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1987, 109, 5975-5982.
2. (b) Dobashi, Y.; Hara, S.; Iitaka, Y. J. Org. Chem. 1988, 53, 3894-3896.
3. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089-5098.
4. (d) Dobashi, Y.; Dobashi, A.; Iitaka, Y. Tetrahedron Lett. 1994, 35, 9413-9416 and references cited therein.
5. (e) Pirkle, W. H.; Murray, P. G.; Rausch, D. J.; McKenna, S. T. J. Org. Chem. 1996, 61, 4769-4774.
6. (f) Pirkle, W. H.; Murray, P. G.; Wilson, S. R. ibid. 1996, 61, 4775-4777.
7. (g) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036-4048 and excellent literature citations made therein.
8. (h) Dearden, D. V.; Dejsupa, C; Liang, Y.; Bradshaw, J. S.; Izatt, R, M. J. Am. Chem. Soc. 1997, 119, 353-359.
9. 2. Dobashi, Y.; Kobayashi, K.; Dobashi, A. Tetrahedron Lett. 1998, 39, 93-96.
10. 3. Dobashi, Y.; Dobashi, A.; Ochiai, H.; Hara, S. J. Am. Chem. Soc. 1990, 112, 6121-6123.
11. max =140.3°) was collected using Cu Kα radiation (λ = 1.54178 Å). 1730 reflections above 3σ(I) level were used in the refinement. The structure was solved by the direct method (SHELXS 86). The methine hydrogen of (S,S)-1 and hydroxyl hydrogen of (S)-2 were located by difference-Fourier map, while the others were included at calculated positions. All hydrogen atoms were refined isotropically in the riding mode. Full matrix least squares refinement with 220 variable parameters led to R = 0.043, Rw = 0.058, and GOF = 0.96.
12. 5. 500 ps of molecular dynamics at 300 K using AMBER* force field (MacroModel V4.5, Department of Chemistry, Columbia University, New York) was carried out. During the dynamics run, intermolecular distance constraint between the hydroxyl protons and imino nitrogens and intramolecular torsion constraint involving the OH bond were applied. 500 conformers obtained by 1 ps of sampling interval were subjected to energy minimization, affording a single conformer of the complex.
13. 6. A conformer of the complex was subjected to the preoptimization by semiempirical PM3 calculation. All geometrical parameters were then optimized at the HF/3-21G(*) level. These calculations were conducted by using a program package SPARTAN 4.0 (Wavefunction Inc. California).
14. 2
15. 3. A total of 3186 unique reflections (2θmax =140.3°) was collected using Cu Kα radiation (λ = 1.54178 Å). 2985 reflections above 3σ(I) level were used in the refinement. The structure was solved by the direct method (SIR 92). The hydroxyl hydrogens of (S)-2 were located by difference-Fourier map, while the others were included at calculated positions. All hydrogen atoms were refined isotropically in the riding mode. Full matrix least squares refinement with 465 variable parameters led to R = 0.042, Rw = 0.054, and GOF = 1.13.
16. 6) of the X-ray crystal structures converged with preserving the hydrogen bonds and proximity between substituents, indicating that the hydrogen-bonded structures were reproducible without the packing effect in the crystalline state.