π Attractive interactions : Can they be modulated?

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 439-440

  Jones, Graham B ^a   Chapman, Brant J ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000063198     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6120     Document Type: Article

References (22)

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3. G. B. Jones, B. J. Chapman, Synthesis 1995, 475, and references cited therein.
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11. G. B. Jones, B. J. Chapman, R. S. Huber and R. Beaty, Tetrahedron: Asymmetry., 1994, 5, 1199;
12. G. B. Jones, S. B. Heaton, Tetrahedron:Asymmetry, 1993, 4, 261;
13. G. B. Jones and R. S. Huber, Synlett, 1993, 367;
14. G. B. Jones and S. B. Heaton, Tetrahedron Lett., 1992, 33, 1693.
15. a) B. Nicholls, H. C. Whiting, J. Chem. Soc. 1959, 551.
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17. 1,4.
18. Cycloadducts 2 were analysed by gradient chiral HPLC (Chiracel OD Column, 0.1-1.25% IPA in Hexanes eluent, 1ml/min flow rate)
19. Replacement of the phenyl group with a cyclohexyl results in a lowering of selectivity in the addition to derived glyoxylates: J. K. Whitesell, R. M. Lawrence, H. -H. Chen, J. Org. Chem. 1986, 51, 4779.
20. Coordinates have been submitted to the Cambridge crystallographic database.
21. Modeling performed using an SGI Power Indigo 2 running Spartan 4.0.3. Multiple confomers were generated by sequential rotation about the bond attaching the benzyl group to the oxazolidinone portion of the auxiliary and were subjected to full geometry minimization. For semi-empirical study of π stacking see: Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C.; J. Org. Chem., 1994, 59, 793.
22. Cycloadditions were performed according to Ref.4, and analyzed by Capillary VPC (30m DB1 column, 175-235°C, 1°C / Min ramp rate)