Synthesis, resolution and structure of axially chiral atropisomeric N- arylimides

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5431-5434

  Shimizu, Ken D ^a   Freyer, Heather O ^a   Adams, Richard D ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

Atropisomers; Resolution; X ray crystal structures

Indexed keywords

AMINE; CARBOXYLIC ACID; IMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034662174     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00835-2     Document Type: Article

References (20)

1. Pu, L. H. Chem. Rev. 1998, 98, 2405-2494.
2. (a) Stanforth, S. Tetrahedron 1998, 54, 263-303.
3. (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
4. (a) Verma, S. M.; Singh, N. D. Aust. J. Chem. 1976, 29, 295-300.
5. (b) Kishikawa, K.; Yoshizaki, K.; Kohmoto, S.; Yamamoto, M.; Yamaguchi, K.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 1997, 1233-1239.
6. (a) Shimizu, K. D.; Dewey, T. M.; Rebek Jr., J. J. Am. Chem. Soc. 1994, 116, 5145-5149.
7. (b) Rebek Jr., J. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255.
8. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc.
9. (b) Osamu, K.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T. J. Org. Chem. 1998, 63, 2634-2640.
10. Ohno, A.; Kunitomo, J.; Kawai, Y.; Kawamoto, T.; Tomishima, M.; Yoneda, F. J. Org. Chem. 1996, 61, 9344-9355.
11. Dai, X.; Wong, A.; Virgil, S. C. J. Org. Chem. 1998, 63, 2597-2600.
12. Moormann, A. E.; Yen, C. H.; Yu, S. Synth. Commun. 1987, 17, 1695-1699.
13. Miller, C. A.; Long, L. M. J. Am. Chem. Soc. 1951, 73, 4895-4898.
14. The barriers of rotation were calculated using MM2 as implemented in the software program MacroModel v5.5 (Mohamadi, F.; Richards, N. G. J.; Cuida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467). The rotational barrier varied greatly with the step angle of the dihedral driver. Accurate values were attained only for small step angles <1°. Larger step angles would jump over the barrier and predict considerably smaller rotational barriers.
15. 10.
16. The discrepancy may be due to the severe distortions in the transition state that lead to significant ΔS contributions to the observed rotational barrier that are not accounted for in the molecular modeling forcefields.
17. 1/n, a=8.667(2) Å, b=9.316(3) Å, c=24.669(4) Å, α=90.00(0)°, β=93.48(2)°, γ=90.00(0)°, Z=4, 3402 reflections, R=0.04395. Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Center, CCDC No. CCDC 139122 for 1 and CCDC 139123 for 2. Copies of this information may be obtained free of charge. www:http://www.ccdc.cam.ac.uk.
18. Mitsunobu, O. Synthesis 1981, 1-28.
19. 2/MeOH).
20. -1. Mp 194°C.